Awakening Sleeping Beauty: Vinyl Esters for Macrolactonization

Macrolactones play a critical role in pharmaceuticals and agrochemicals. Numerous efforts have been devoted to developing synthetic methods for them. We highlighted a recent progress for building macrocycles (≥ 12‐membered) via bench‐stable vinyl ester (VE) intermediates, which have been underdevelo...

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Bibliographic Details
Published in:Chinese journal of chemistry 2021-04, Vol.39 (4), p.1022-1024
Main Authors: Song, Qi, Kong, Luyao, Zhu, Lili, Hong, Ran, Huang, Sha‐Hua
Format: Article
Language:English
Subjects:
Acetylene
Agrochemicals
Amide bond
Chemical synthesis
Esters
Intermediates
Macrolactonization
Racemization
Vinyl ester
Vinyl esters
Ynamide
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Summary:Macrolactones play a critical role in pharmaceuticals and agrochemicals. Numerous efforts have been devoted to developing synthetic methods for them. We highlighted a recent progress for building macrocycles (≥ 12‐membered) via bench‐stable vinyl ester (VE) intermediates, which have been underdeveloped for half century. These methods are mild and racemization‐free and warrant wide recognition in macrocyclization as the key step in complex molecule synthesis. The renaissance of two half‐century‐old acyl donors, derived from AVEs and ynamines or ynamides, reminds us that the reactivities of specific functional groups are still waiting to be explored. The macrocyclization via the vinyl ester intermediates is mild, racemization‐free, and an ease of work‐up due to readily depletion of ester or amide derived from the coupling reagent. This novel approach is complementary to other macrolactonization methods and thus are of great expectation to future application.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.202000571