The Mukaiyama type aldol reaction for the synthesis of -2,6-disubstituted tetrahydropyrans: synthesis of diospongin A and B

An efficient synthesis protocol for the preparation of trans -2,6-disubstituted tetrahydropyrans by the reaction of 1-phenyl-1-triemthylsiloxyethylene with six membered cyclic hemiacetals in the presence of iodine is developed. This reaction proceeds smoothly under mild conditions employing a cataly...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-10, Vol.17 (41), p.9169-9181
Main Authors: Bharath, Yada, Choudhury, Utkal Mani, Sadhana, N, Mohapatra, Debendra K
Format: Article
Language:English
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Summary:An efficient synthesis protocol for the preparation of trans -2,6-disubstituted tetrahydropyrans by the reaction of 1-phenyl-1-triemthylsiloxyethylene with six membered cyclic hemiacetals in the presence of iodine is developed. This reaction proceeds smoothly under mild conditions employing a catalytic amount of molecular iodine. The feature of this novel conversion includes milder reaction conditions, broader substrate scope, functional group tolerance and good diastereoselectivity. The efficiency and practicality of the current method were successfully displayed in the total synthesis of diospongin A and B in good yields. The synthesis of 2,6- trans -disubstituted tetrahydropyrans following the Mukaiyama type aldol reaction through C-C bond formation demonstrates the practicality of this protocol in the total synthesis of diospongin A and B.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01549c