A divergent strategy to gabosines featuring a switchable two-way aldol cyclization
Organic and Biomolecular Chemistry(2019)
摘要
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.
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