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
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.