A NOVEL, STEREOSELECTIVE SYNTHESIS OF CIS-4A (S), 8A(R)-DECAHYDRO-6(2H)-ISOQUINOLONES FROM MEROQUINENE ESTERS

Authors
MARTINELLI MJ PETERSON BC KHAU VV HUTCHISON DR SULLIVAN KA
Citation
Mj. Martinelli et al., A NOVEL, STEREOSELECTIVE SYNTHESIS OF CIS-4A (S), 8A(R)-DECAHYDRO-6(2H)-ISOQUINOLONES FROM MEROQUINENE ESTERS, Tetrahedron letters, 34(34), 1993, pp. 5413-5416
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
34
Year of publication
1993
Pages
5413 - 5416
Database
ISI
SICI code
0040-4039(1993)34:34<5413:ANSSOC>2.0.ZU;2-C
Abstract
Intramolecular cyclization of N-acylated meroquinene t-butyl esters in cold H2SO4 cleanly afforded cis-4a(S), 8a(R)-decahydro-6(2H)-isoquino lones with complete stereocontrol in >95% yield. Formation of the mero quinene esters from cinchona alkaloid autoxidation using an improved D oering protocol was accomplished in three steps with 85% overall yield .