FORMATION OF HETEROCYCLES BY THE MITSUNOBU REACTION - STEREOSELECTIVESYNTHESIS OF (-ALPHA-SKYTANTHINE())

Authors
TSUNODA T OZAKI F SHIRAKATA N TAMAOKA Y YAMAMOTO H ITO S
Citation
T. Tsunoda et al., FORMATION OF HETEROCYCLES BY THE MITSUNOBU REACTION - STEREOSELECTIVESYNTHESIS OF (-ALPHA-SKYTANTHINE()), Tetrahedron letters, 37(14), 1996, pp. 2463-2466
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
14
Year of publication
1996
Pages
2463 - 2466
Database
ISI
SICI code
0040-4039(1996)37:14<2463:FOHBTM>2.0.ZU;2-F
Abstract
Cyanomethylenetributylphosphorane was shown to mediate the dehydrocycl ization of diols and amino alcohols to give the corresponding 6-member ed O- and N-heterocycles in 90% or better yields. Using the reaction a s a key step, (+)-alpha-skytanthine, a unique mono terpene alkaloid wa s synthesized stereoselectively. Copyright (C) 1996 Elsevier Science L td