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Please login to access the full content or check if you have access via Variation 1: The Corey–Nicolaou Method

DOI: 10.1055/sos-SD-020-01369

Maier, M. E.Science of Synthesis, (2007201456.

The CoreyNicolaou method is based on the use of pyridine-2-thiol esters 125 that are formed in situ from the ω-hydroxy acids 123.[‌146‌] Protonation of the basic nitrogen by the hydroxy group activates the thioester and positions the nucleophilic oxygen in close proximity to the carboxy group. The tetrahedral intermediate 126 subsequently collapses to the desired lactone 127 and pyridine-2-thione (Scheme 53). The intermediate pyridine-2-thiol esters can be obtained from the ω-hydroxy esters, 2,2-dipyridyl disulfide (124), ­using triphenylphosphine in xylene.

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