Total Synthesis of (−)-Callystatin A

A convergent enantioselective synthesis of the natural product (−)-callystatin A (1) is described. Key features of the synthesis include a lipase-mediated kinetic resolution to install the C5 lactone stereochemistry, a hydrozirconation-based approach to the C8−C9 trisubstituted (Z)-olefin, and a ste...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 6; no. 18; pp. 3203 - 3206
Main Authors Langille, Neil F, Panek, James S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.09.2004
Amer Chemical Soc
Subjects
Alkenes - chemical synthesis
Alkenes - chemistry
Animals
Catalysis
Chemistry
Chemistry, Organic
Fatty Acids, Unsaturated - chemical synthesis
Fatty Acids, Unsaturated - chemistry
Molecular Structure
Physical Sciences
Porifera - chemistry
Science & Technology
Stereoisomerism
Tin - chemistry
ALCOHOLS
RING-CLOSING METATHESIS
CALLYSTATIN-A
ALDEHYDES
ASYMMETRIC TOTAL-SYNTHESIS
CHROMIUM(II)-MEDIATED SYNTHESIS
POTENT CYTOTOXIC POLYKETIDE
STEREOSELECTIVE SYNTHESIS
PARTICIPATION
MARINE SPONGE
Online AccessGet full text

Cover

More Information
Summary:A convergent enantioselective synthesis of the natural product (−)-callystatin A (1) is described. Key features of the synthesis include a lipase-mediated kinetic resolution to install the C5 lactone stereochemistry, a hydrozirconation-based approach to the C8−C9 trisubstituted (Z)-olefin, and a stereoselective cross-coupling of a vinyl dibromide to install the C14−C15 trisubstituted (E)-olefin.
Bibliography:Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol048664r