First Stereoselective Total Synthesis of Anti-Inflammatory Metabolite­ Penicillinolide A

Mopuri Sudhakar Reddy; Gembali Manikanta; Palakodety Radha Krishna

doi:10.1055/s-0037-1611040

Synthesis, Table of Contents

Synthesis 2019; 51(06): 1427-1434
DOI: 10.1055/s-0037-1611040

paper

First Stereoselective Total Synthesis of Anti-Inflammatory Metabolite Penicillinolide A

Mopuri Sudhakar Reddy

^aOrganic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India

^bAcademy of Scientific and Innovative Research (AcSIR), New Delhi 110025, India Email: prkgenius@iict.res.in

,

Gembali Manikanta

^aOrganic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India

,

Palakodety Radha Krishna *

^aOrganic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India

› Author Affiliations

Abstract

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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.

Key words

Jacobsen’s hydrolytic kinetic resolution (HKR) - chelation controlled allylation - Brown’s asymmetric allylation - hydroboration - Yamaguchi lactonization

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References

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Supplementary Material

Supporting Information

First Stereoselective Total Synthesis of Anti-Inflammatory Metabolite­ Penicillinolide A

First Stereoselective Total Synthesis of Anti-Inflammatory Metabolite Penicillinolide A