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A unified and straightforward total synthesis of (+)-porantheridine and (−)-6-epi-porantheridine

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Abstract

A unified asymmetric total synthesis of (+)-porantheridine and (−)-6-epi-porantheridine has been accomplished. The two molecules were prepared via a Horner–Wadsworth–Emmons/aza-Michael addition reaction or diastereoselective nucleophilic substitution of 2-methoxypiperidine from a common intermediate, respectively. The key features of the unified synthetic strategy also included an asymmetric addition of silyl dienolate to sulfinylimine, substrate-controlled reduction, Wacker oxidation and TFA-promoted cyclization.

Graphical abstract: A unified and straightforward total synthesis of (+)-porantheridine and (−)-6-epi-porantheridine

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Publication details

The article was received on 24 Dec 2018, accepted on 20 Mar 2019 and first published on 04 Apr 2019


Article type: Research Article
DOI: 10.1039/C8QO01398E
Citation: Org. Chem. Front., 2019, Advance Article

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    A unified and straightforward total synthesis of (+)-porantheridine and (−)-6-epi-porantheridine

    J. Wang, W. Li, L. Liu, B. Wang, Y. Zhou, S. Huang and X. Wang, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01398E

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