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

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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

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Publication details

The article was received on 17 Oct 2019, accepted on 13 Nov 2019 and first published on 20 Nov 2019


Article type: Edge Article
DOI: 10.1039/C9SC05252F
Chem. Sci., 2020, Advance Article
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    Total synthesis of (−)-penicimutanin a and related congeners

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

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