ABNORMAL 8-MEMBERED RING FORMATION THROUGH S(N)2' INTRAMOLECULAR NOZAKI KISHI REACTION IN A SYNTHETIC APPROACH TO A TAXANE PRECURSOR/

Authors
MULLER B FEREZOU JP LALLEMAND JY PANCRAZI A PRUNET J PRANGE T
Citation
B. Muller et al., ABNORMAL 8-MEMBERED RING FORMATION THROUGH S(N)2' INTRAMOLECULAR NOZAKI KISHI REACTION IN A SYNTHETIC APPROACH TO A TAXANE PRECURSOR/, Tetrahedron letters, 39(3-4), 1998, pp. 279-282
Citations number
36
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
3-4
Year of publication
1998
Pages
279 - 282
Database
ISI
SICI code
0040-4039(1998)39:3-4<279:A8RFTS>2.0.ZU;2-U
Abstract
Two different reactions were experimented for the construction of the eight-membered B-ring of taxane skeleton through the formation of the C9-C10 bond A SmI2 promoted radical reaction on seco-alkynyl aldehydes 11cis or 11trans failed. A Nozaki/Kishi reaction carried out on the s eco-iodovinyl aldehyde 12trans led, through an unprecedented intramole cular S(N)2' reaction, to the ''abnormally'' cyclised product 14, the structure of which has been confirmed by X-ray crystallography. (C) 19 97 Elsevier Science Ltd. All rights reserved.