Synthesis 2019; 51(06): 1427-1434
DOI: 10.1055/s-0037-1611040
paper
© Georg Thieme Verlag Stuttgart · New York

First Stereoselective Total Synthesis of Anti-Inflammatory Metabolite­ Penicillinolide A

Mopuri Sudhakar Reddy
a   Organic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
b   Academy of Scientific and Innovative Research (AcSIR), New Delhi 110025, India   Email: prkgenius@iict.res.in
,
Gembali Manikanta
a   Organic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
,
a   Organic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
› Author Affiliations
Further Information

Publication History

Received: 21 August 2018

Accepted after revision: 27 September 2018

Publication Date:
14 November 2018 (online)


IICT/Pubs/2018/205

Abstract

The first asymmetric total synthesis of penicillinolide A is described. Key steps of the synthesis involve Jacobsen’s hydrolytic kinetic resolution (HKR), chelation controlled allylation, Brown’s asymmetric allylation, hydroboration, and Yamaguchi lactonization.

Supporting Information

 
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