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

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

doi:10.1016/S0040-4039(02)02430-9

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

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

Chemistry

Research output: Contribution to journal › Article › peer-review

5 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 language	English
Pages (from-to)	9559-9560
Number of pages	1
Journal	Tetrahedron Letters
Volume	43
DOIs	https://doi.org/10.1016/S0040-4039(02)02430-9
Publication status	Published - 2002

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

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.",

author = "Adams, \{J. A. S.\} and S. Clunas and Alan Turner",

year = "2002",

doi = "10.1016/S0040-4039(02)02430-9",

language = "English",

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journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - Synthesis and preliminary odour evaluation of 5a-androst-16-en-7-one: a new androstenone analogue

AU - Adams, J. A. S.

AU - Clunas, S.

AU - Turner, Alan

PY - 2002

Y1 - 2002

N2 - 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.

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.

U2 - 10.1016/S0040-4039(02)02430-9

DO - 10.1016/S0040-4039(02)02430-9

M3 - Article

SN - 0040-4039

VL - 43

SP - 9559

EP - 9560

JO - Tetrahedron Letters

JF - Tetrahedron Letters

ER -

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

Abstract

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