VITAMIN-B-12-CATALYZED C,C-BOND FORMATION - SYNTHESIS OF JASMONATES VIA SEQUENTIAL RADICAL REACTION

Authors
BUSATO S SCHEFFOLD R
Citation
S. Busato et R. Scheffold, VITAMIN-B-12-CATALYZED C,C-BOND FORMATION - SYNTHESIS OF JASMONATES VIA SEQUENTIAL RADICAL REACTION, Helvetica Chimica Acta, 77(1), 1994, pp. 92-99
Citations number
42
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
77
Issue
1
Year of publication
1994
Pages
92 - 99
Database
ISI
SICI code
0018-019X(1994)77:1<92:VCF-SO>2.0.ZU;2-T
Abstract
The Cbl-catalyzed electroreduction of 3-(2'-bromo-1'-ethoxyethoxy)cycl openten (la) in presence of 1-cyanovinyl-acetate (8) gave, in a sequen tial radical reaction (5-exo-trig-cyclization of 1a followed by additi on to 8), thoxy-hexahydro-2'H-cyclopenta[b]furan-4'-yl)ethyl acetate ( 10a). This intermediate was transformed to methyl jasmonate (7; four s teps) and epituberolide (9; three steps) in 20 and 31% yield, respecti vely, from cyclopent-2-en-1-ol.