Abstract
Reexamination of the synthesis of (3β,5α,14α)-3-hydroxy-14-methylcholest-7-en-15-one has led to an improved, large-scale preparation of this ketone. Noteworthy is the controlled outcome of a solvent effect observed during the pinacol-type rearrangement of vinyl epoxide 18 and the use of the ethoxyethyl ether protecting group at the C3 alcohol during alkylation. Preparative-scale routes to ergostenone derivatives 3 and 4 and pregnenone analogue 5 are described.
Original language | English |
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Pages (from-to) | 4047-4053 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 51 |
Issue number | 21 |
DOIs | |
State | Published - Oct 1 1986 |