Journal of Medicinal Chemistry p. 1054 - 1058 (1980)
Update date:2022-08-05
Topics:
Jarvis, Bruce B.
Stahly, G. Patrick
Pavanasasivam, Gowsala
Mazzola, Eugene P.
Verrucarin A (2) was epoxidized to give the β-9,10-epoxide 7 (major product) and α-9,10-epoxide 9 (minor product).The β-epoxide 7 and its acetate 8 exhibit high in vivo antileukemic activity against P-388 mouse leukemia, whereas 2 and 9 are inactive.Epoxidation of verrucarin B (3) and roridin A (1) to their respective β-9,10-epoxides (11 and 12, respectively) also yields compounds with substantially increased activity.Allylic alcohols derived from 2, α-C8 (20), β-C8 (14), and C16 (15), were synthesized and tested; only 15 exhibited substantial in vivo activity.
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Doi:10.1055/s-1980-28993
(1980)Doi:10.1134/S1070428020090201
(2020)Doi:10.1021/ol049126h
(2004)Doi:10.1016/j.bmcl.2007.06.010
(2007)Doi:10.1002/jhet.3050
(2018)Doi:10.1021/ja00536a060
(1980)