Synlett 2020; 31(16): 1598-1602
DOI: 10.1055/s-0040-1707215
letter
© Georg Thieme Verlag Stuttgart · New York

Concise Total Synthesis of (+)-Atlanticone C

Johanna Proessdorf
,
Andreas Zech
,
Christian Jandl
,
Thorsten Bach
Department Chemie and Catalysis Research Center (CRC), Technische Universität München, 85747 Garching, Germany   Email: thorsten.bach@ch.tum.de
› Author Affiliations
This project was supported by the DeutscheForschungsgemeinschaft (Ba 1372/22-1) and by the TUM Graduate School.
Further Information

Publication History

Received: 27 May 2020

Accepted after revision: 24 June 2020

Publication Date:
31 July 2020 (online)


Abstract

The first enantioselective total synthesis of (+)-atlanticone C is described. The complex tricyclic protoilludane core was rapidly assembled by a photochemical reaction cascade starting from an easily accessible indanone precursor (3 steps). Optimization of an enantioselective Corey–Bakshi–Shibata reduction permitted a catalytic chiral reso­lution of the racemic photoproduct (45% over two steps; up to 98% ee). The enantiomerically enriched photoproduct was efficiently transformed into the (+)-enantiomer of atlanticone C (10 steps; 18% yield), and the absolute configuration of naturally occurring (–)-atlanticone C was thereby determined.

Supporting Information

Primary Data

 
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