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
Open Access Status
Volume 45
Issue 4
Start page 1177
End page 1186
Total pages 10
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)
Collection: Scopus Import - Archived
 
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