A Total Synthesis of the Antifungal Deoxyaminocyclitol Nabscessin B from l -(+)-Tartaric Acid

Xiang Ma; Qiao Yan; Martin G. Banwell; Jas S. Ward

doi:10.1021/acs.orglett.7b03495

A Total Synthesis of the Antifungal Deoxyaminocyclitol Nabscessin B from l -(+)-Tartaric Acid

Xiang Ma, Qiao Yan, Martin G. Banwell^*, Jas S. Ward

^*Corresponding author for this work

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

16 Citations (Scopus)

Abstract

Aminocyclitol 2, a recently isolated and notable antifungal agent, was prepared from homochiral Î-hydroxycyclohexenone 4, which is itself available in six steps from l-(+)-tartaric acid (3). The well-defined rigidifying effect arising from the 1,2-diacetal protecting group associated with compound 4 and its derivatives allows for high levels of regio- and stereo-chemical control in the manipulation of the cyclitol framework.

Original language	English
Pages (from-to)	142-145
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.7b03495
Publication status	Published - 5 Jan 2018

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AU - Banwell, Martin G.

AU - Ward, Jas S.

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AB - Aminocyclitol 2, a recently isolated and notable antifungal agent, was prepared from homochiral Î-hydroxycyclohexenone 4, which is itself available in six steps from l-(+)-tartaric acid (3). The well-defined rigidifying effect arising from the 1,2-diacetal protecting group associated with compound 4 and its derivatives allows for high levels of regio- and stereo-chemical control in the manipulation of the cyclitol framework.

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A Total Synthesis of the Antifungal Deoxyaminocyclitol Nabscessin B from l -(+)-Tartaric Acid

Abstract

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