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

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

Publication History

Received: 12 May 2023

Accepted: 10 August 2023

Accepted Manuscript online:
10 August 2023

Article published online:
16 October 2023

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