Literature DB >> 24882888

Concise total synthesis of (±)-actinophyllic acid.

Brett A Granger1, Ivan T Jewett1, Jeffrey D Butler1, Stephen F Martin1.   

Abstract

A concise total synthesis of the complex indole alkaloid (±)-actinophyllic acid was accomplished by a sequence of reactions requiring only 10 steps from readily-available, known starting materials. The approach featured a Lewis acid-catalyzed cascade of reactions involving stabilized carbocations that delivered the tetracyclic core of the natural product in a single chemical operation. Optimal conversion of this key intermediate into (±)-actinophyllic acid required judicious selection of a protecting group strategy.

Entities:  

Keywords:  Cascade Reaction; Iminium Ion; Mannich-type Reaction; Total Synthesis

Year:  2014        PMID： 24882888      PMCID： PMC4034156          DOI： 10.1016/j.tet.2014.03.034

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


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8.  Synthesis of (±)-actinophyllic acid and analogs: applications of cascade reactions and diverted total synthesis.

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