NOVEL SYNTHESES OF CAMPTOTHECIN ALKALOIDS .2. CONCISE SYNTHESIS OF (S)-CAMPTOTHECINS

Authors
FORTUNAK JMD KITTERINGHAM J MASTROCOLA AR MELLINGER M SISTI NJ WOOD JL ZHUANG ZP
Citation
Jmd. Fortunak et al., NOVEL SYNTHESES OF CAMPTOTHECIN ALKALOIDS .2. CONCISE SYNTHESIS OF (S)-CAMPTOTHECINS, Tetrahedron letters, 37(32), 1996, pp. 5683-5686
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
32
Year of publication
1996
Pages
5683 - 5686
Database
ISI
SICI code
0040-4039(1996)37:32<5683:NSOCA.>2.0.ZU;2-N
Abstract
A g-step, convergent total synthesis of(S)-camptothecin alkaloids is d escribed. The intramolecular [4+2] cycloaddition of an N-arylimidate w ith an alkyne is used to prepare the alkaloid ABC ring system.(1) The chiral center is derived utilizing Seebach's chemistry(2) for the dias tereoselective Michael addition of a chiral dioxolanone enolate to a m ethylene malonate acceptor. The total synthesis of non-racemic topotec an is accomplished from (S)-10-hydroxycamptothecin in an additional st ep. Copyright (C) 1996 Elsevier Science Ltd