HIGHLY EFFICIENT SYNTHESIS OF THE NATURAL SPIRO-TERPENOID (+ -)-ANDIROLACTONE/

Authors
ORDUNA A ZEPEDA LG TAMARIZ J
Citation
A. Orduna et al., HIGHLY EFFICIENT SYNTHESIS OF THE NATURAL SPIRO-TERPENOID (+ -)-ANDIROLACTONE/, Synthesis, (4), 1993, pp. 375-377
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
4
Year of publication
1993
Pages
375 - 377
Database
ISI
SICI code
0039-7881(1993):4<375:HESOTN>2.0.ZU;2-F
Abstract
A synthesis of the natural terpenoid spirolactone (+/-)-andirolactone (1) is described. Condensation of dimethyl malonate (9) with 1-acetyl- 4-methyl-3-cyclohexen-1-ol (3), prepared by Diels-Alder reaction of ol efin 5 and isoprene (4), and thermal decarboxylation of the resulting spirolactone 10, afforded 1 in 46 % overall yield.