STEREOSELECTIVE SYNTHESIS OF TA-(P-BROMOPHENYL)-17-ACETYLGONA-1,3,4(10)-TRIENES

Authors
BURTIN G PELLISSIER H SANTELLI M
Citation
G. Burtin et al., STEREOSELECTIVE SYNTHESIS OF TA-(P-BROMOPHENYL)-17-ACETYLGONA-1,3,4(10)-TRIENES, Tetrahedron, 54(28), 1998, pp. 8065-8074
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
28
Year of publication
1998
Pages
8065 - 8074
Database
ISI
SICI code
0040-4020(1998)54:28<8065:SSOT>2.0.ZU;2-Z
Abstract
Titanium tetrachloride mediated dialkylation of methyl 4-p-bromophenyl -4-oxobutanoate ethylene ketals 2 by 1,8-bis(trimethylsilyl)-2,6-octad iene 1 (BISTRO) led to a mixture of methyl dl and omophenyl-2,5-diviny lcyclopentan-1-yl)-propanoates 3. Iodolactonisation, reduction with Bu 3SnH, Jones oxidation, methoxycarbonylation, alkylation by iodobenzocy clobutene, demethoxycarbonylation and then pyrolysis led to the title compounds. (C) 1998 Elsevier Science Ltd. All rights reserved.