METALATED ALPHA-ALKOXYPROPARGYL AND GAMMA-ALKOXYALLENYL DERIVATIVES -APPLICATIONS IN SOME ALDOL REACTIONS TOWARDS DITERPENE SYNTHESIS

Authors
ANIES C LALLEMAND JY PANCRAZI A
Citation
C. Anies et al., METALATED ALPHA-ALKOXYPROPARGYL AND GAMMA-ALKOXYALLENYL DERIVATIVES -APPLICATIONS IN SOME ALDOL REACTIONS TOWARDS DITERPENE SYNTHESIS, Tetrahedron letters, 37(31), 1996, pp. 5519-5522
Citations number
41
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
31
Year of publication
1996
Pages
5519 - 5522
Database
ISI
SICI code
0040-4039(1996)37:31<5519:MAAGD->2.0.ZU;2-M
Abstract
The allenyl titanium 11a, prepared using Yamamoto's conditions reacted with different aldehydes 12a-c to produce the anti acetylenic diols 1 3a-c. In a synthetic approach to erigerol 1 this reaction was applied to the aldehyde 4 and the expected key intermediate 13d was obtained i n 40% yield after removal of the THP group. During this study the alph a-alkoxypropargylstannane 14 and the alpha-alkoxyallenylstannane 15 we re prepared in good yields alter transmetallation of the corresponding lithio derivatives 5b and 7b by Ti((OPr)-Pr-i)(4) or Et(2)ZnCl. Copyr ight (C) 1996 Elsevier Science Ltd