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Issue 16, 2019
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A divergent strategy to synthesize gabosines featuring a switchable two-way aldol cyclization

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Abstract

Gabosines and their natural analogues, belonging to C7 carbasugars, have attracted great attention in synthesis due to their rich structural variety and promising biological activities. A new diversity-oriented approach for the gabosine-type carbasugars based on a tunable regioselective aldol cyclization of flexible precursor 2 is explored. Two cyclization modes (A and B) of the precursor can be well controlled by switching promoters to selectively produce two resulting cyclohexa(e)nones 3 and 10, both of which are versatile intermediates for various C7 carbasugars. After the conversion of 3 to eight natural carbasugars, the utility of intermediate 10 is illustrated by the first synthesis of (−)-gabosine L, as well as the new synthesis of (−)-gabosine A, (−)-gabosine B, (−)-gabosine N and (−)-gabosine O. The chemical structure and the absolute configuration of (−)-gabosine L are confirmed by its total synthesis.

Graphical abstract: A divergent strategy to synthesize gabosines featuring a switchable two-way aldol cyclization

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Publication details

The article was received on 25 Feb 2019, accepted on 22 Mar 2019 and first published on 23 Mar 2019


Article type: Paper
DOI: 10.1039/C9OB00469F
Org. Biomol. Chem., 2019,17, 4061-4072

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    A divergent strategy to synthesize gabosines featuring a switchable two-way aldol cyclization

    X. Yang, P. Yuan, F. Shui, Y. Zhou and X. Chen, Org. Biomol. Chem., 2019, 17, 4061
    DOI: 10.1039/C9OB00469F

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