Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2005(0): 0006-0006
DOI: 10.1055/s-2005-865342
DOI: 10.1055/s-2005-865342
Synthesis of Natural Products and Drugs
© Georg Thieme Verlag Stuttgart · New York
Total Synthesis of (-)-Aurisides A and B
Contributor(s): Philip KocienskiI. 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
Cambridge University, UK
Stereocontrolled Total Synthesis of (-)-Aurisides A and B
Angew. Chem. Int. Ed. 2005, 44: 1130-1133
Further Information
Publication History
Publication Date:
20 July 2005 (online)
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.