First Total Synthesis of (±)-Strychnofoline via a Highly Selective Ring-Expansion Reaction
- 22 November 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (50) , 14826-14827
- https://doi.org/10.1021/ja027906k
Abstract
An efficient synthesis of the antitumor alkaloid (±)-strychnofoline is documented. Key to the development of the highly convergent strategy delineated is the coupling of a cyclic imine with spiro[cyclopropan-1,3‘-oxindole], which takes place in a highly diastereoselective manner. The ability to conduct annulation reactions of spirocyclopropyloxindoles with functionalized cyclic imines provides new avenues for the preparation of this important class of biologically active structures.Keywords
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