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

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Abstract

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.

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

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Publication details

The article was received on 12 Jul 2019, accepted on 30 Sep 2019 and first published on 30 Sep 2019


Article type: Paper
DOI: 10.1039/C9OB01549C
Org. Biomol. Chem., 2019, Advance Article

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

    Y. Bharath, U. M. Choudhury, N. Sadhana and D. K. Mohapatra, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB01549C

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