A Convergent Synthesis of (+)-Cryptophycin B, a Potent Antitumor Macrolide from Nostoc sp. Cyanobacteria

An efficient and highly stereoselective synthesis of cryptophycin B (2), a potent cytotoxic agent, is described. The ester-derived titanium-enolate-mediated syn-aldol reaction was employed to generate the stereocenters C(5) and C(6). The route is convergent and provides a convenient access to the sy...

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Bibliographic Details
Published inOrganic letters Vol. 2; no. 11; pp. 1573 - 1575
Main Authors Ghosh, Arun K, Bischoff, Alexander
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.06.2000
Amer Chemical Soc
Subjects
Antifungal Agents - chemical synthesis
Antifungal Agents - chemistry
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Chemistry
Chemistry, Organic
Cyanobacteria - chemistry
Depsipeptides
Dipeptides - chemical synthesis
Dipeptides - chemistry
Macrolides - chemical synthesis
Macrolides - chemistry
Marine Biology
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
ENOLATE ALDOL REACTION
ESTER
CYTOTOXIC DEPSIPEPTIDE
SPONGE DYSIDEA-ARENARIA
ANALOGS
ANTI-ALDOLS
CRYPTOPHYCIN-A
ARENASTATIN-A
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Summary:An efficient and highly stereoselective synthesis of cryptophycin B (2), a potent cytotoxic agent, is described. The ester-derived titanium-enolate-mediated syn-aldol reaction was employed to generate the stereocenters C(5) and C(6). The route is convergent and provides a convenient access to the synthesis of structural variants of cryptophycin B as well as members of its family.
Bibliography:Medline
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol000058i