TOTAL SYNTHESES OF (-ACUTIPHYCIN AND (+)-TRANS-20,21-DIDEHYDROACUTIPHYCIN())

Authors
SMITH AB CHEN SSY NELSON FC REICHERT JM SALVATORE BA
Citation
Ab. Smith et al., TOTAL SYNTHESES OF (-ACUTIPHYCIN AND (+)-TRANS-20,21-DIDEHYDROACUTIPHYCIN()), Journal of the American Chemical Society, 119(45), 1997, pp. 10935-10946
Citations number
46
Categorie Soggetti
Chemistry
Journal title
Journal of the American Chemical Society → ACNP
ISSN journal
00027863
Volume
119
Issue
45
Year of publication
1997
Pages
10935 - 10946
Database
ISI
SICI code
0002-7863(1997)119:45<10935:TSO(A(>2.0.ZU;2-W
Abstract
The first total syntheses of the cytotoxic macrolides (+)-acutiphycin (1) and (+)-trans-20,21-didehydroacutiphycin (2) have been achieved. A n acyclic stereocontrol strategy was employed to establish the configu rations at C(5), C(10), and C(13) as well as the E geometry of the C(8 ,9)-trisubstituted olefin. Importantly, the natural source of 1 and 2, the blue-green alga Osillatoria acutissima, no longer produces these metabolites.