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

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Date

2017

Authors

Ma, Xiang
Gao, Yuqian (Nadia)
Banwell, Martin
Carr, Paul D
Willis, Anthony

Journal Title

Journal ISSN

Volume Title

Publisher

American Chemical Society

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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Keywords

Citation

URI

http://hdl.handle.net/1885/219195

Collections

ANU Research Publications

Source

Journal of Organic Chemistry

Type

Journal article

Book Title

Entity type

Access Statement

Open Access

License Rights

DOI

10.1021/acs.joc.7b00340

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Total Synthesis of (±)-3-O-Demethylmacronine R1.pdf (332.46 KB)

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