SYNTHESIS OF (+ -)-STERPURENE AND HYDROXYLATED DERIVATIVES BY 1,6-ADDITION OF ORGANOCUPRATES TO ACCEPTOR-SUBSTITUTED ENYNES/

Authors
KRAUSE N
Citation
N. Krause, SYNTHESIS OF (+ -)-STERPURENE AND HYDROXYLATED DERIVATIVES BY 1,6-ADDITION OF ORGANOCUPRATES TO ACCEPTOR-SUBSTITUTED ENYNES/, Liebigs Annalen der Chemie, (5), 1993, pp. 521-525
Citations number
34
Categorie Soggetti
Chemistry
Journal title
Liebigs Annalen der Chemie → ACNP
ISSN journal
01702041
Issue
5
Year of publication
1993
Pages
521 - 525
Database
ISI
SICI code
0170-2041(1993):5<521:SO(-AH>2.0.ZU;2-1
Abstract
The synthesis of (+/-)-sterpurene (1), 14-/15-hydroxysterpurene (13), and 11,14-/11,15-dihydroxysterpurene (14) is described. Key steps are the 1,6-addition of lithium dimethylcuprate to the 2-en-4-ynoate 11 an d the regioselective trapping of the allenyl enolate with methyl trifl ate. The vinylallene 6 thus obtained undergoes an intramolecular Diels -Alder reaction to give the tricyclic ester 5, which serves as a commo n precursor of 1, 13, and 14,