Total Synthesis of (-)-Aurisides A and B

doi:10.1055/s-2005-865342

Synfacts 2005(0): 0006-0006
DOI: 10.1055/s-2005-865342

Synthesis of Natural Products and Drugs

Total Synthesis of (-)-Aurisides A and B

Rezensent(en): Philip Kocienski

I. Paterson*, G. J. Florence, A. C. Heimann, A. C. MacKay
Cambridge University, UK
Stereocontrolled Total Synthesis of (-)-Aurisides A and B
Angew. Chem. Int. Ed. 2005, 44: 1130-1133

Abstract

Volltext

als PDF herunterladen

Key words

glycosylation - asymmetric vinylogous Mukaiyama aldol -

Significance

The first synthesis of Aurisides A and B is reported. The Aurisides are isolated from the sea hare Dolabella auricularia. They are cytotoxic towards HeLa S₃ cervical cancer cell lines with IC₅₀ values of 0.17 and 1.2 µm mL^-1, respectively.

Comment

Variations on the aldol reaction were used to synthesize and link the C1-C7 and C8-C17 fragments of the aglycone. The asymmetric vinylogous Mukaiyama-directed aldol reaction mediated by an (R)-binol-Ti(O-i-Pr)₄ species (89%, ee = 94%) is noteworthy.

Abbildungen