SYNTHESIS OF NOR-AMBREINOLIDE FROM (-CIS-ABIENOL())

Authors
BARRERO AF SANCHEZ JF ALVAREZMANZANEDA EJ ALTAREJOS J MUNOZ M HAIDOUR A
Citation
Af. Barrero et al., SYNTHESIS OF NOR-AMBREINOLIDE FROM (-CIS-ABIENOL()), Tetrahedron, 50(22), 1994, pp. 6653-6662
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
22
Year of publication
1994
Pages
6653 - 6662
Database
ISI
SICI code
0040-4020(1994)50:22<6653:SONF(>2.0.ZU;2-L
Abstract
The synthesis of nor-ambreinolide (2) from cis-abienol (1) was carried out by direct treatment with OsO4-NaIO4 or RuO4-NaIO4. The oxymercuri ation-demercuriation of I led to a mixture of 8,12-epoxylabdanes (5-17 ) which was also converted into nor-ambreinolide by treatment with RuO 4-NaIO4. The formation pathways of such epoxy derivatives are discusse d.