Corey–Nicolaou macrolactonization
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Through Organic chemistry
Mechanism
The hydroxy acid first reacts with the 2,2'-Dipyridyldisulfide to form the corresponding 2-pyridinethiol ester, and after a proton transfer, the alkoxide attacks the carbonyl carbon, forming a tetrahedral transition state, before resolving back to the desired lactone and 2-pyridinethione.
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Variants
Other heterocyclic disulfides have been used in place of 2,2'-dipyridyldisulfide.
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