Total Synthesis of (−)-Archazolid B

A highly convergent synthesis of archazolid B, a potent and highly selective V-ATPase inhibitor, is described. A relay ring-closing metathesis reaction was used to form the 24-membered macrocyclic lactone, whereas the sensitive cis-triene moiety of the archazolids was assembled with a modified Still...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 129; no. 29; pp. 8960 - 8961
Main Authors Roethle, Paul A, Chen, Ingrid T, Trauner, Dirk
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.07.2007
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Multidisciplinary
Indicators and Reagents
Macrolides - chemistry
Myxococcales - chemistry
Physical Sciences
Ruthenium
Science & Technology
Stereoisomerism
Thiazoles - chemistry
RING-CLOSING METATHESIS
STRATEGY
ESTERS
CHEMISTRY
OLEFIN METATHESIS
ARCHAZOLID-A
ARCHANGIUM-GEPHYRA
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Summary:A highly convergent synthesis of archazolid B, a potent and highly selective V-ATPase inhibitor, is described. A relay ring-closing metathesis reaction was used to form the 24-membered macrocyclic lactone, whereas the sensitive cis-triene moiety of the archazolids was assembled with a modified Stille coupling.
Bibliography:istex:D55A04A7E30B88D484EF3B2CFA7391D937EC98A3
ark:/67375/TPS-3B7RL548-F
Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0733033