Literature DB >> 15876077

An N-acyliminium cyclization approach to a total synthesis of (+)-cylindricine C.

Jia Liu1, Jacob J Swidorski, Scott D Peters, Richard P Hsung.   

Abstract

[reaction: see text] Details of problems and solutions encountered during the development of an enantioselective total synthesis of (+)-cylindricine C are described here. The total synthesis itself was accomplished in 8 steps, featuring an N-acyliminium cyclization strategy, the seldom-used Wharton rearrangement, and a key epimerization at C5.

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Year:  2005        PMID: 15876077     DOI: 10.1021/jo0501846

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  3 in total

Review 1.  Studies on total synthesis of the cylindricine/fasicularin/lepadiformine family of tricyclic marine alkaloids.

Authors:  Steven M Weinreb
Journal:  Chem Rev       Date:  2006-06       Impact factor: 60.622

2.  Aza-[3 + 3] Annulations: A New Unified Strategy in Alkaloid Synthesis.

Authors:  Grant S Buchanan; John B Feltenberger; Richard P Hsung
Journal:  Curr Org Synth       Date:  2010-08-01       Impact factor: 1.975

3.  Catalytic, asymmetric indolizidinone aza-quaternary stereocenter synthesis: expedient synthesis of the cylindricine alkaloid core.

Authors:  Derek M Dalton; Tomislav Rovis
Journal:  Org Lett       Date:  2013-04-30       Impact factor: 6.005

  3 in total

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