DIALKYLATION OF 2,3-BUTANEDIONE DIKETAL WITH 1,8-BIS(TRIMETHYLSILYL)-2,6-OCTADIENE (BISTRO) - APPLICATION TO THE SYNTHESIS OF ESTRONE DERIVATIVES

Authors
PELLISSIER H SANTELLI M
Citation
H. Pellissier et M. Santelli, DIALKYLATION OF 2,3-BUTANEDIONE DIKETAL WITH 1,8-BIS(TRIMETHYLSILYL)-2,6-OCTADIENE (BISTRO) - APPLICATION TO THE SYNTHESIS OF ESTRONE DERIVATIVES, Tetrahedron, 52(27), 1996, pp. 9093-9100
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
27
Year of publication
1996
Pages
9093 - 9100
Database
ISI
SICI code
0040-4020(1996)52:27<9093:DO2DW1>2.0.ZU;2-O
Abstract
Titanium tetrachloride mediated-dialkylation of 2,3-butanedione ketal 2 by 1,8-bis(trimethylsilyl)-2,6-octadiene (BISTRO) 1 led to 1-acetyl- 1-methyl-2,5-divinylcyclopentane 4. This latter was methoxycarbonylate d (NaH/dimethylcarbonate) and then alkylated with iodobenzocyclobutene (Cs2CO3/acetone) to give a benzocyclobutenic intermediate 6, whose th ermolysis provided the 12-oxo-estrane derivatives 8 - 11. Copyright (C ) 1996 Elsevier Science Ltd