Organotin and -mercury routes to enones, dienones amd spiroacetals

O'Shea M.G. and Kitching W. (1989) Organotin and -mercury routes to enones, dienones amd spiroacetals. Tetrahedron, 45 4: 1177-1186. doi:10.1016/0040-4020(89)80026-2

Author O'Shea M.G.
Kitching W.
Title Organotin and -mercury routes to enones, dienones amd spiroacetals
Journal name Tetrahedron   Check publisher's open access policy
ISSN 0040-4020
Publication date 1989-01-01
Sub-type Article (original research)
DOI 10.1016/0040-4020(89)80026-2
Volume 45
Issue 4
Start page 1177
End page 1186
Total pages 10
Language eng
Subject 1303 Specialist Studies in Education
3002 Drug Discovery
1605 Policy and Administration
Abstract Conjugate addition of trinethyltinlithium to cyclohex-2-enone followed by enolate trapping with alkylating agents provide traus-2-alkyl-3-trimethylstannylcyclohexanones, which on reaction with Grignard reagents derived from 4-bromo-1-butene or 5-bromo-1-pentene afford tertiary γ-stannylcyclohexanols in a highly diastereoselective fashion. Triaethylstannyl-triggered ring fragmentation (by lead tetraacetate in benzene) leads efficiently to dienones, which on hydroxymercuration, cyclisation and reduction provide a range of 1,6-dioxaspiro[4.5]decanes and 1,7-dioxaspiro[5,5]undecanes, some of which are of insect origin. Epoxidation of these dienones, followed by acid catalysed hydrolysis and cyclisation leads to hydroxy substituted spiroacetals. Syntheses of 6-oxononan-1-ol (a glandular component of the fruit flies, D. halfordiae and D. occipitalis) and E-6-nonene-2-one, which is transformed readily into exo or endo-brevicomin, are also presented. Some dialkyl substituted [4.5]- and [5.5] spiroacetals have been acquired also by free radical addition reactions etc., utilising organomercury chemistry.
Q-Index Code C1
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
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