Prins Cyclization: Novel Strategy towards the Diastereoselective Total Synthesis of (–)-Cryptocaryolone

Dhanraj O. Biradar; Yogesh D. Mane; Jhillu Singh Yadav; Basi V. Subba Reddy

doi:10.1055/a-2152-0671

Synthesis, Table of Contents

Synthesis 2023; 55(24): 4163-4172
DOI: 10.1055/a-2152-0671

paper

Prins Cyclization: Novel Strategy towards the Diastereoselective Total Synthesis of (–)-Cryptocaryolone

Dhanraj O. Biradar

^aIndian Institute of Chemical Technology, Hyderabad 500007, Telangana, India

^bMaharashtra Mahavidyalaya, Nilanga 413521, Dist. Latur, M.S., India

,

Yogesh D. Mane

^cBSS Arts, Science & Commerce College, Makni, Tq. Lohara 413604, Dist. Osmanabad, M.S., India

,

Jhillu Singh Yadav∗

^aIndian Institute of Chemical Technology, Hyderabad 500007, Telangana, India

,

Basi V. Subba Reddy∗

^aIndian Institute of Chemical Technology, Hyderabad 500007, Telangana, India

› Author Affiliations

Abstract

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Abstract

A highly diastereoselective total synthesis of TBDPS-protected (–)-cryptocaryolone has been achieved in 12 linear steps with an overall yield of 7.1%, following a recently developed Prins cyclization strategy for the construction of trans-2,6-disubstituted 3,4-dihydropyrans. Another key intermediate, i.e. syn-1,3-diol, was prepared by the Wacker oxidation followed by a hydroxyl-directed syn-reduction of the keto functionality. In this report, the versatility of Prins cyclization in the total synthesis of TBDPS-protected (–)-cryptocaryolone is demonstrated. The key steps involved in the approach are Prins cyclization for the construction of the trans-2,6-disubstituted dihydropyran, Wacker oxidation and a hydroxyl-directed syn-reduction reaction.

Key words

Prins cyclization - Wacker oxidation - hydroxyl-directed syn-reduction - cryptocaryolone - bicyclic lactones

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References

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