Synthetic Applications of Prins Cyclization in Natural Product Syntheses

Chem Rec. 2022 Aug;22(8):e202200044. doi: 10.1002/tcr.202200044. Epub 2022 May 9.

Abstract

The natural products having tetrahydropyran unit with multiple chiral centers serve as magnificent building blocks for various active pharmaceutical ingredients (APIs). 'Prins cyclization is one of the wonderful strategies to construct tetrahydropyran unit stereoselectively in asymmetric synthesis. In this account, we discuss our research efforts toward the synthesis of various natural products from the past two decades (2005-2020) by using Prins cyclization as a key step. Further, the synthetic utility of this reaction was investigated and well demonstrated on various molecules successfully.

Keywords: Chiral pool; Natural products; Prins reaction; Tetrahyropyran; Total synthesis.

Publication types

  • Review

MeSH terms

  • Biological Products*
  • Cyclization
  • Molecular Structure
  • Stereoisomerism

Substances

  • Biological Products