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Synlett 2013; 24(10): 1303-1306
DOI: 10.1055/s-0033-1338447
DOI: 10.1055/s-0033-1338447
letter
Formal Synthesis of Aspidospermidine via the Intramolecular Cascade Transannular Cyclization
Further Information
Publication History
Received: 28 February 2013
Accepted after revision: 30 March 2013
Publication Date:
08 May 2013 (online)
Abstract
A formal synthesis of aspidospermidine is reported through a novel preparation of Stork’s penultimate tricyclic ketone intermediate. The key steps of the synthesis consist of an intramolecular cascade transannular cyclization, triggered by the removal of Boc group, which simultaneously forms the C, D, and E rings of aspidospermidine and conveniently setting up the quaternary stereocenter via decarboxylative alkylation reaction of the β-keto ester.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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Syntheses of nonracemic aspidospermidine:
Syntheses of racemic aspidospermidine:
After we originally reported the discovery of this cascade cyclization,6a Tu and Lei also observed the similar cyclization in their total syntheses of lycojapodine A, see: