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

Ma, Xiang; Yan, Qiao; Banwell, Martin; Ward, Jas

Description

Aminocyclitol 2, a recently isolated and notable antifungal agent, was prepared from homochiral γ-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.

CollectionsANU Research Publications
Date published: 2018
Type: Journal article
URI: http://hdl.handle.net/1885/176968
Source: Organic Letters
DOI: 10.1021/acs.orglett.7b03495
Access Rights: Open Access

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