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Selective acetylation of sterols in imidazole-functionalized surfactant vesicles

✍ Scribed by Robert A. Moss; Yukihisa Okumura

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 294 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)93487-2

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✦ Synopsis

In imidazole-functionalized surfactant coaggregates, acetyl groups are stereoselectively transferred from R-nitrophenyl acetate to 36 vs 3a-cholestanol, and regioselectively transferred to 38 vs 6p-cholestanol.

There have been studies of stereoselectivity attending the degradative esterolyses of chiral substrates in micellar or vesicular aggregates, 1.2 but there have been relatively few reports of synthetic selective reactions in these media. Apposite examples include peptide coupling reactions in the interior water pools of reverse micelles,3 the oxymercuration of dienes in (aqueous) anionic micelles, 4a the hydroboration of enones in cationic micelles,bb and the epoxidation or hydroxylation of sterols in steroidal porphyrin/phospholipid/substrate coaggregates.5

Recently, we found that coaggregates of cholesterol and the N,E-dihexadecylcholine ester

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