The synthesis of 9-alpha, 11-alpha-epoxy-5-alpha-cholest-7-ene-3-beta,5,6-beta-triol(1), a a highly oxygenated marine sterol containing a 9,11-epoxide moiety in the nucleus, is described. Epoxy sterol 1 was synthesized from cholesta-5,7-dien-3-beta-ol. Oxidation of this sterol with m-chloroperbenzoic acid followed by hydrolysis and acetylation furnished 5-alpha-cholesst-7-ene-3-beta,5, 6-alpha-triol 3,6-diacetate (2). Mercuric acetate dehydrogenation of diacetate 2, followed by oxidation with manganese dioxide and epoxidation with m-chloroperbenzoic acid, afforded 9-alpha,11-alpha-epoxy-3-beta, 5-alpha-cholest-7en-6-one (5). Reduction of 5 with lithium aluminum hydride gave the desired compound 1. The structures of all synthetic intermediates were confirmed by H-1 and C-13 nuclear magnetic resonance (NMR) spectroscopy. A reassignment of resonances for carbons 1, 8, and 15 in the C-13 NMR spectrum of 1, based on 2D-NMR correlation spectroscopy, has been accomplished
SYNTHESIS OF THE MARINE EPOXY STEROL 9-ALPHA,11-ALPHA-EPOXY-5-ALPHA-CHOLEST-7-ENE-3-BETA,5,6-BETA-TRIOL / Migliuolo, A.; Notaro, G.; Piccialli, Vincenzo; Sica, D.. - In: STEROIDS. - ISSN 0039-128X. - STAMPA. - 56:(1991), pp. 154-158. [10.1016/0039-128X(91)90066-5]
SYNTHESIS OF THE MARINE EPOXY STEROL 9-ALPHA,11-ALPHA-EPOXY-5-ALPHA-CHOLEST-7-ENE-3-BETA,5,6-BETA-TRIOL
PICCIALLI, VINCENZO;
1991
Abstract
The synthesis of 9-alpha, 11-alpha-epoxy-5-alpha-cholest-7-ene-3-beta,5,6-beta-triol(1), a a highly oxygenated marine sterol containing a 9,11-epoxide moiety in the nucleus, is described. Epoxy sterol 1 was synthesized from cholesta-5,7-dien-3-beta-ol. Oxidation of this sterol with m-chloroperbenzoic acid followed by hydrolysis and acetylation furnished 5-alpha-cholesst-7-ene-3-beta,5, 6-alpha-triol 3,6-diacetate (2). Mercuric acetate dehydrogenation of diacetate 2, followed by oxidation with manganese dioxide and epoxidation with m-chloroperbenzoic acid, afforded 9-alpha,11-alpha-epoxy-3-beta, 5-alpha-cholest-7en-6-one (5). Reduction of 5 with lithium aluminum hydride gave the desired compound 1. The structures of all synthetic intermediates were confirmed by H-1 and C-13 nuclear magnetic resonance (NMR) spectroscopy. A reassignment of resonances for carbons 1, 8, and 15 in the C-13 NMR spectrum of 1, based on 2D-NMR correlation spectroscopy, has been accomplishedI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
