REARRANGEMENT REACTIONS OF AROMADENDRANE DERIVATIVES - THE SYNTHESIS OF (-MAALIOL, STARTING FROM NATURAL (+)-AROMADENDRENE-IV())

Authors
GIJSEN HJM WIJNBERG JBPA VANRAVENSWAAY C DEGROOT A
Citation
Hjm. Gijsen et al., REARRANGEMENT REACTIONS OF AROMADENDRANE DERIVATIVES - THE SYNTHESIS OF (-MAALIOL, STARTING FROM NATURAL (+)-AROMADENDRENE-IV()), Tetrahedron, 50(16), 1994, pp. 4733-4744
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
16
Year of publication
1994
Pages
4733 - 4744
Database
ISI
SICI code
0040-4020(1994)50:16<4733:RROAD->2.0.ZU;2-E
Abstract
Starting from the hydroazulene alpha-ketol 6, which can easily be prep ared from (+)-aromadendrene (1), two different routes to hydronaphthal ene compounds with a maaliane skeleton have been developed, both proce eding in high overall yield. The first route leads to cis-fused maalia ne derivatives; the second one offers access to trans-fused maaliane s esquiterpenes, as demonstrated in this paper in the synthesis of (+)-m aaliol (5).