ASYMMETRIC-SYNTHESIS OF ALKANNIN AND SHIKONIN

Authors
COULADOUROS EA PLYTA ZF STRONGILOS AT PAPAGEORGIOU VP
Citation
Ea. Couladouros et al., ASYMMETRIC-SYNTHESIS OF ALKANNIN AND SHIKONIN, Tetrahedron letters, 38(41), 1997, pp. 7263-7266
Citations number
41
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
41
Year of publication
1997
Pages
7263 - 7266
Database
ISI
SICI code
0040-4039(1997)38:41<7263:AOAAS>2.0.ZU;2-L
Abstract
A new general and convergent route for the synthesis of the title comp ounds is presented. The polyoxygenated aromatic ring system is annulat ed in one operation by the condensation of a Michael type acceptor wit h an 1,4 dipole equivalent. The chiral center of the target is introdu ced via an asymmetric allyl boration in high ee. Overall, the fully pr otected natural product is constructed within 8 steps in 35% total yie ld. (C) 1997 Elsevier Science Ltd.