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Published on: November 30, 2022
A --> J prostaglandin swap: a new tactic for cyclopentenone prostaglandin synthesis
Giuseppe Zanoni1, Francesca Castronovo, Eleonora Perani
1Dipartimento di Chimica Organica, Università di Pavia, Via Taramelli 10, 27100 Pavia, Italy. gzanoni@unipv.itgzanoni@unipv.it
Abstract:
A practical methodology for the synthesis of J-type prostaglandins has been developed starting from the well-consolidated approaches established for the synthesis of A-type prostaglandins. An efficient 1,3-allylic transposition of the C-9 hydroxyl group of intermediate 4 furnished the advanced precursor 5 for J(2) synthesis. Our optimized A-J swap protocol employed selenium chemistry, involving the [2,3] sigmatropic rearrangement of secondary allylic selenoxide 11a.
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