The Corey-Seebach Reagent in the 21st Century: A Review

Molecules. 2023 May 26;28(11):4367. doi: 10.3390/molecules28114367.

Abstract

The Corey-Seebach reagent plays an important role in organic synthesis because of its broad synthetic applications. The Corey-Seebach reagent is formed by the reaction of an aldehyde or a ketone with 1,3-propane-dithiol under acidic conditions, followed by deprotonation with n-butyllithium. A large variety of natural products (alkaloids, terpenoids, and polyketides) can be accessed successfully by utilizing this reagent. This review article focuses on the recent contributions (post-2006) of the Corey-Seebach reagent towards the total synthesis of natural products such as alkaloids (lycoplanine A, diterpenoid alkaloids, etc.), terpenoids (bisnorditerpene, totarol, etc.), polyketide (ambruticin J, biakamides, etc.), and heterocycles such as rodocaine and substituted pyridines, as well and their applications towards important organic synthesis.

Keywords: Corey-Seebach reagent; alkaloids; natural products.

Publication types

  • Review

MeSH terms

  • Alkaloids*
  • Biological Products*
  • Indicators and Reagents
  • Polyketides*
  • Terpenes

Substances

  • Indicators and Reagents
  • Alkaloids
  • Polyketides
  • Terpenes
  • Biological Products

Grants and funding

The research was partly financed by research projects: Siedlce University of Natural Sciences and Humanities (UPH/WNSP/ICH/zadaniebadawcze/143/23/B), Medical University of Lublin (DS 730).