Synthesis of the trans-syn-trans perhydrobenz[e]indene moiety of the stellettins and of the stelliferins

Authors
Raeppel, F Weibel, JM Heissler, D
Citation
F. Raeppel et al., Synthesis of the trans-syn-trans perhydrobenz[e]indene moiety of the stellettins and of the stelliferins, TETRAHEDR L, 40(35), 1999, pp. 6377-6381
Citations number
40
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
35
Year of publication
1999
Pages
6377 - 6381
Database
ISI
SICI code
0040-4039(19990827)40:35<6377:SOTTPM>2.0.ZU;2-D
Abstract
The perhydrobenz[e]indene moiety of the stellettins and of the stelliferins , two families of isomalabaricane-type triterpenes with trans-syn-trans rin g junctions, has been built from a bicyclic gamma,delta-unsaturated aldehyd e by a reaction sequence including a Lewis acid catalysed ene cyclisation t o form a cyclopentanol, a hydroxyl-directed cyclopropanation, and the ring opening of a cyclopropyl ketone with trimethylsilyl iodide. (C) 1999 Elsevi er Science Ltd. All rights reserved.