A NEW APPROACH TO THE SYNTHESIS OF PODOPHYLLOTOXIN BASED ON EPIMERIZATION REACTIONS

Authors
MEDARDE M RAMOS AC CABALLERO E LOPEZ JL DECLAIRAC RPL SANFELICIANO A
Citation
M. Medarde et al., A NEW APPROACH TO THE SYNTHESIS OF PODOPHYLLOTOXIN BASED ON EPIMERIZATION REACTIONS, Tetrahedron letters, 37(15), 1996, pp. 2663-2666
Citations number
62
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
15
Year of publication
1996
Pages
2663 - 2666
Database
ISI
SICI code
0040-4039(1996)37:15<2663:ANATTS>2.0.ZU;2-R
Abstract
A formal synthesis of podophyllotoxin has been achieved by means of th e well known conjugate addition-alkylation of 5H-furan-2-one, followed by cyclization and controlled epimerizations. This approach represent s a useful new route to the 8,7'-trans-stereochemistry of aryltetralin lactones, that in other methodologies requires the opening and reclos ure of the lacton ring. Copyright (C) 1996 Elsevier Science Ltd