A convergent synthesis of (+)-cryptophycin B, a potent antitumor macrolide from Nostoc sp. cyanobacteria.
[structure--see text] 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.
Ghosh
A K
AK
Department of Chemistry, University of Illinois at Chicago, 60607, USA. arunghos@uic.edu
Bischoff
A
A
D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D000458:Cyanobacteria / Q000737:chemistry; D047630:Depsipeptides; D004151:Dipeptides / Q000138:chemical synthesis / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis / Q000737:chemistry; D008386:Marine Biology; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000935:Antifungal Agents; D000970:Antineoplastic Agents; D047630:Depsipeptides; D004151:Dipeptides; D018942:Macrolides; D010456:Peptides, Cyclic; C088419:cryptophycin; C410204:cryptophycin B