Synlett 2018; 29(07): 856-862
DOI: 10.1055/s-0036-1591938
synpacts
© Georg Thieme Verlag Stuttgart · New York

Biomimetic Approaches: Synthesis of (±)-Homodimericin A

Donghui Ma
University at Albany, State University of New York, 1400 Washington Ave., Albany, NY 12222, USA   Email: zwang9@albany.edu
,
University at Albany, State University of New York, 1400 Washington Ave., Albany, NY 12222, USA   Email: zwang9@albany.edu
› Author Affiliations
Start-up funds from SUNY-Albany are greatly acknowledged.
Further Information

Publication History

Received: 19 December 2017

Accepted after revision: 25 January 2018

Publication Date:
19 February 2018 (online)

In memory of Professors Gilbert Stork and Ronald Breslow

Abstract

A brief history of biomimetic total synthesis is reviewed. The molecules covered in this SynPact account include tropinone (Robinson, 1917), usnic acid (Barton, 1956), progesterone (Johnson, 1971), endiandric acids (Nicolaou, 1982), methyl homosecodaphniphyllate (Heathcock, 1988), glabrescol (Corey, 2000), FR182877 (Sorensen, 2002 and Evans, 2002), and intricarene (Pattenden, 2006 and Trauner, 2006). Key biomimetic transformations of the syntheses are highlighted. Our recent biomimetic synthesis of homodimericin A is also discussed. Our study validates the key steps of the biosynthesis proposed by Clardy et al.

 
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