A Total Synthesis of (±)-3-O-Demethylmacronine through Rearrangement of a Precursor Embodying the Haemanthidine Alkaloid Framework

Xiang Ma; Nadia Gao; Martin G. Banwell; Paul D. Carr; Anthony C. Willis

doi:10.1021/acs.joc.7b00340

A Total Synthesis of (±)-3-O-Demethylmacronine through Rearrangement of a Precursor Embodying the Haemanthidine Alkaloid Framework

Xiang Ma, Nadia Gao, Martin G. Banwell^*, Paul D. Carr, Anthony C. Willis

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

A total synthesis of the racemic modification, (±)-2, of the tazettine-type alkaloid 3-O-demethylmacronine is described. The key steps are an intramolecular Alder-ene (IMAE) reaction and a lactam-to-lactone rearrangement of tetracycle 13, a compound that embodies the haemanthidine alkaloid framework.

Original language	English
Pages (from-to)	4336-4341
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	82
Issue number	8
DOIs	https://doi.org/10.1021/acs.joc.7b00340
Publication status	Published - 21 Apr 2017

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abstract = "A total synthesis of the racemic modification, (±)-2, of the tazettine-type alkaloid 3-O-demethylmacronine is described. The key steps are an intramolecular Alder-ene (IMAE) reaction and a lactam-to-lactone rearrangement of tetracycle 13, a compound that embodies the haemanthidine alkaloid framework.",

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AU - Ma, Xiang

AU - Gao, Nadia

AU - Banwell, Martin G.

AU - Carr, Paul D.

AU - Willis, Anthony C.

PY - 2017/4/21

Y1 - 2017/4/21

N2 - A total synthesis of the racemic modification, (±)-2, of the tazettine-type alkaloid 3-O-demethylmacronine is described. The key steps are an intramolecular Alder-ene (IMAE) reaction and a lactam-to-lactone rearrangement of tetracycle 13, a compound that embodies the haemanthidine alkaloid framework.

AB - A total synthesis of the racemic modification, (±)-2, of the tazettine-type alkaloid 3-O-demethylmacronine is described. The key steps are an intramolecular Alder-ene (IMAE) reaction and a lactam-to-lactone rearrangement of tetracycle 13, a compound that embodies the haemanthidine alkaloid framework.

UR - https://www.scopus.com/pages/publications/85018464587

U2 - 10.1021/acs.joc.7b00340

DO - 10.1021/acs.joc.7b00340

M3 - Article

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EP - 4341

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JF - Journal of Organic Chemistry

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ER -

A Total Synthesis of (±)-3-O-Demethylmacronine through Rearrangement of a Precursor Embodying the Haemanthidine Alkaloid Framework

Abstract

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