(Q42147079)

English

Total synthesis of tetrahydrolipstatin and stereoisomers via a highly regio- and diastereoselective carbonylation of epoxyhomoallylic alcohols.

scientific article published on 18 July 2014

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scholarly article

1 reference

Europe PubMed Central

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8 March 2020

Total synthesis of tetrahydrolipstatin and stereoisomers via a highly regio- and diastereoselective carbonylation of epoxyhomoallylic alcohols (English)

1 reference

Europe PubMed Central

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8 March 2020

diastereoselectivity

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based on heuristic

inferred from title

George A O'Doherty

5

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8 March 2020

author name string

Michael Mulzer

1

1 reference

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8 March 2020

Brandon J Tiegs

2

1 reference

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8 March 2020

Yanping Wang

3

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8 March 2020

Geoffrey W Coates

4

1 reference

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8 March 2020

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publication date

18 July 2014

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8 March 2020

Journal of the American Chemical Society

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8 March 2020

136

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8 March 2020

10814-10820

1 reference

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8 March 2020

30

1 reference

Europe PubMed Central

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8 March 2020

Cryptocaryol Structure-Activity Relationship Study of Cancer Cell Cytotoxicity and Ability to Stabilize PDCD4

1 reference

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29 May 2018

High sensitivity of Giardia duodenalis to tetrahydrolipstatin (orlistat) in vitro

1 reference

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29 May 2018

Convergent de novo synthesis of vineomycinone B2 methyl ester

1 reference

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29 May 2018

Cryptocaryols A and B: total syntheses, stereochemical revision, structure elucidation, and structure-activity relationship

1 reference

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29 May 2018

Structure Activity Relationship Study of the Cleistriosides and Cleistetrosides for Antibacterial/Anticancer Activity.

1 reference

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Improving the affinity of SL0101 for RSK using structure-based design.

1 reference

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29 May 2018

C3'/C4'-Stereochemical Effects of Digitoxigenin α-L-/α-D-Glycoside in Cancer Cytotoxicity

1 reference

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29 May 2018

The fatty acid synthase inhibitor orlistat reduces experimental metastases and angiogenesis in B16-F10 melanomas

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

29 May 2018

Transition-metal-catalyzed synthesis of aspergillide B: an alkyne addition strategy

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

29 May 2018

Synthesis and biological investigation of the β-thiolactone and β-lactam analogs of tetrahydrolipstatin

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

29 May 2018

De novo asymmetric synthesis of fridamycin E.

1 reference

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29 May 2018

A de novo approach to the synthesis of glycosylated methymycin analogues with structural and stereochemical diversity

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

29 May 2018

A concise, phosphate-mediated approach to the total synthesis of (-)-tetrahydrolipstatin

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

29 May 2018

Asymmetric synthesis of anti-aldol segments via a nonaldol route: synthetic applications to statines and (-)-tetrahydrolipstatin

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

29 May 2018

Self-consistent synthesis of the squalene synthase inhibitor zaragozic acid C via controlled oligomerization

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

29 May 2018

Tetrahydrolipstatin analogues as modulators of endocannabinoid 2-arachidonoylglycerol metabolism

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

29 May 2018

Synthesis of novel beta-lactone inhibitors of fatty acid synthase

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

29 May 2018

Crystal structure of the thioesterase domain of human fatty acid synthase inhibited by Orlistat

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

29 May 2018

Inhibition of fatty acid synthase induces endoplasmic reticulum stress in tumor cells.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

29 May 2018

De novo formal synthesis of (-)-apicularen A via an iterative asymmetric hydration sequence

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

29 May 2018

Total synthesis and comparative analysis of orlistat, valilactone, and a transposed orlistat derivative: Inhibitors of fatty acid synthase

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

29 May 2018

Antitumoral actions of the anti-obesity drug orlistat (XenicalTM) in breast cancer cells: blockade of cell cycle progression, promotion of apoptotic cell death and PEA3-mediated transcriptional repression of Her2/neu (erbB-2) oncogene

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

29 May 2018

Synthesis of beta-lactones: a highly active and selective catalyst for epoxide carbonylation

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

29 May 2018

Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. I. Producing organism, fermentation, isolation and biological activity

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

29 May 2018

Inhibition of fatty acid synthase by Orlistat accelerates gastric tumor cell apoptosis in culture and increases survival rates in gastric tumor bearing mice in vivo

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

17 August 2018

Chromium(III) octaethylporphyrinato tetracarbonylcobaltate: a highly active, selective, and versatile catalyst for epoxide carbonylation

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

17 August 2018

Orlistat is a novel inhibitor of fatty acid synthase with antitumor activity

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

17 August 2018

Synthesis of beta-lactones by the regioselective, cobalt and Lewis acid catalyzed carbonylation of simple and functionalized epoxides

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4120994

17 August 2018

Asymmetric synthesis of (-)-tetrahydrolipstatin: an anti-aldol-based strategy

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Enzymatic Lactonization Stategy for Enantioselective Synthesis of a Tetrahydrolipstatin Synthon

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

[Lewis acid]+[Co(CO)(4)]- complexes: a versatile class of catalysts for carbonylative ring expansion of epoxides and aziridines

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

A highly practical and enantioselective reagent for the allylation of aldehydes

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Oxazoline N-oxide-mediated [2+3] cycloadditions. Application to a synthesis of (-)-tetrahydrolipstatin

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Palladium-catalyzed DYKAT of butadiene monoepoxide: enantioselective total synthesis of (+)-DMDP, (-)-bulgecinine, and (+)-broussonetine G

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Sequencing of three-component olefin metatheses: total synthesis of either (+)-gigantecin or (+)-14-deoxy-9-oxygigantecin

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

The mechanism of epoxide carbonylation by [Lewis Acid]+[Co(CO)4]- catalysts

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Practical beta-lactone synthesis: epoxide carbonylation at 1 atm

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Carbonylation of heterocycles by homogeneous catalysts

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Catalytic double carbonylation of epoxides to succinic anhydrides: catalyst discovery, reaction scope, and mechanism

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Formal total synthesis of neopeltolide

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

The lipase inhibitor tetrahydrolipstatin binds covalently to the putative active site serine of pancreatic lipase

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

De novo asymmetric synthesis of cladospolide B-D: structural reassignment of cladospolide D via the synthesis of its enantiomer

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

A stereodivergent synthesis of all stereoisomers of centrolobine: control of selectivity by a protecting-group manipulation

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

MNBA-mediated β-lactone formation: mechanistic studies and application for the asymmetric total synthesis of tetrahydrolipstatin

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Regioselective carbonylation of trans-disubstituted epoxides to β-lactones: a viable entry into syn-aldol-type products

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

A stereoselective synthesis of (-)-tetrahydrolipstatin

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. II. Chemistry and structure elucidation

1 reference

https://pubmed.ncbi.nlm.nih.gov/25004122

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Identifiers

10.1021/JA505639U

1 reference

Europe PubMed Central

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8 March 2020

release_c64th7s7krecbekbw52iuflbli

1 reference

https://api.fatcat.wiki/v0/release/c64th7s7krecbekbw52iuflbli

24 November 2022

based on heuristic

mapped directly with Wikidata item

1 reference

Europe PubMed Central

https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:25004122%20AND%20SRC:MED&resulttype=core&format=json

8 March 2020

1 reference

Europe PubMed Central

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8 March 2020

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