Synthesis and preliminary odour evaluation of 5a-androst-16-en-7-one: a new androstenone analogue

J. A. S. Adams, S. Clunas, Alan Turner

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

5alpha-Androst-16-en-3-one has been prepared from 5alpha-androstane-7,17-dione in a five-step sequence, via selective ketalisation at C-7 with bis-trimethylsilyloxyethane and trimethylsilyl triflate as the key step, followed by introduction of the Delta(16) bond by reaction of the 17-hydrazone with iodine to give the vinyl iodide, and deiodination with sodium in ethanol, with acid-catalysed deprotection of the 7-oxo group as the final step. The compound has a mild sandalwood odour. (C) 200 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)9559-9560
Number of pages1
JournalTetrahedron Letters
Volume43
DOIs
Publication statusPublished - 2002

Cite this

Synthesis and preliminary odour evaluation of 5a-androst-16-en-7-one: a new androstenone analogue. / Adams, J. A. S.; Clunas, S.; Turner, Alan.

In: Tetrahedron Letters, Vol. 43, 2002, p. 9559-9560.

Research output: Contribution to journalArticle

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AB - 5alpha-Androst-16-en-3-one has been prepared from 5alpha-androstane-7,17-dione in a five-step sequence, via selective ketalisation at C-7 with bis-trimethylsilyloxyethane and trimethylsilyl triflate as the key step, followed by introduction of the Delta(16) bond by reaction of the 17-hydrazone with iodine to give the vinyl iodide, and deiodination with sodium in ethanol, with acid-catalysed deprotection of the 7-oxo group as the final step. The compound has a mild sandalwood odour. (C) 200 Elsevier Science Ltd. All rights reserved.

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