학술논문

Total synthesis of (-)- and (+)-balanol
Document Type
Academic Journal
Source
Journal of Organic Chemistry. July 12, 1996, Vol. 61 Issue 14, p4572, 10 p.
Subject
Plant metabolites -- Research
Organic compounds -- Synthesis
Biological sciences
Chemistry
Language
ISSN
0022-3263
Abstract
A method for the synthesis of (-)- and (+)-balanol involves stereospecific functionalization of N-benzyl-epsilon-caprolactam for the production of core aminohydroxyazepane subunit in racemic form. The production of both enantiomers of balanol depends on resolution prior to coupling to the benzophenone subunit. Another method involves silicon-controlled cyclization of (2S,3R)-3-hydroxylysine followed by reduction. Balanol is a fungal metabolite that inhibits protein kinase C.