Citation
Jd. White et Yg. Choi, Catalyzed asymmetric Diels-Alder reaction of benzoquinone. Total synthesisof (-)-ibogamine, ORG LETT, 2(15), 2000, pp. 2373-2376
Citations number
32
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060
→ ACNP
Volume
2
Issue
15
Year of publication
2000
Pages
2373 - 2376
Database
ISI
SICI code
1523-7060(20000727)2:15<2373:CADROB>2.0.ZU;2-O
Abstract
[GRAPHICS]
The Diets-Alder addition of diene 2 with benzoquinone catalyzed by (S)-BINO
L-TiCl2 produced cycloadduct 5 in >65% yield and 87% ee. The cycloadduct wa
s transformed into (-)-ibogamine in nine steps (10% overall yield from benz
oquinone). A model for the transition state leading to 5 is proposed.