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Synlett 2018; 29(07): 856-862
DOI: 10.1055/s-0036-1591938
DOI: 10.1055/s-0036-1591938
synpacts
Biomimetic Approaches: Synthesis of (±)-Homodimericin A
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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