Issue 3, 2020

Total synthesis of (−)-penicimutanin a and related congeners

Abstract

The first total synthesis of penicimutanin A (1) was achieved within 10 steps (LLS). Key innovations in this synthesis consist of (1) a highly efficient electro-oxidative dearomatization; (2) an unprecedented bisoxirane-directed intermolecular aldol reaction from the sterically hindered face of the ketone and (3) the diastereoselective one-step Meerwein–Eschenmoser–Claisen rearrangement enabling the construction of vicinal quaternary stereocenters. Related family members e.g. penicimutanolone (3) and penicimutatin (5) have also been synthesized alongside, elucidating their absolute configurations, hence the absolute configuration of 1.

Graphical abstract: Total synthesis of (−)-penicimutanin a and related congeners

Supplementary files

Article information

Article type
Edge Article
Submitted
17 Oct 2019
Accepted
13 Nov 2019
First published
20 Nov 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 656-660

Total synthesis of (−)-penicimutanin a and related congeners

H. Yu, Y. Zong and T. Xu, Chem. Sci., 2020, 11, 656 DOI: 10.1039/C9SC05252F

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