Prins cyclization: new strategy for the stereoselective total synthesis of Polyrhacitide A
Dhanraj O Biradar1,2, Yogesh D Mane3, Jhillu S Yadav1
1Chemistry, Indian Institute of Chemical Technology, Hyderabad, India.
Abstract:
A highly stereoselective total synthesis of polyrhacitide A, a polyketide natural product, has been accomplished by means of Prins cyclisation. The key precursor i.e. anti-1,3-diol for polyrhacitide A has been prepared from trans-2,6-disubstituted-3,4-dihydropyrans. In this approach, Prins cyclisation has successfully been utilised twice for the construction of 1,3-diol unit of polyrhacitide A. The key steps involved in this approach are Jacobsen hydrolytic kinetic resolution, Mitsunobu inversion, Prins cyclisation and Ring-closing metathesis (RCM).
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