The Corey-Seebach Reagent in the 21st Century: A Review-Reference-Cited by-同舟云学术

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

Published:2023-05-26 Issue:11 Volume:28 Page:4367
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Haroon Muhammad¹,Zahoor Ameer Fawad¹^ORCID,Ahmad Sajjad²,Mansha Asim¹^ORCID,Irfan Muhammad³,Mushtaq Aqsa¹,Akhtar Rabia¹⁴^ORCID,Irfan Ali¹^ORCID,Kotwica-Mojzych Katarzyna⁵,Mojzych Mariusz⁶^ORCID

Affiliation:

1. Medicinal Chemistry Research Lab, Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan

2. Department of Chemistry, University of Engineering and Technology Lahore, Faisalabad Campus, Faisalabad 38000, Pakistan

3. Department of Pharmaceutics, Government College University Faisalabad, Faisalabad 38000, Pakistan

4. Department of Chemistry, Superior University, Faisalabad 38000, Pakistan

5. Laboratory of Experimental Cytology, Medical University of Lublin, Radziwiłłowska 11, 20-080 Lublin, Poland

6. Department of Chemistry, Siedlce University of Natural Sciences and Humanities, 3-Go Maja 54, 08-110 Siedlce, Poland

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.

Funder

Siedlce University of Natural Sciences and Humanities

Medical University of Lublin

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

Link

https://www.mdpi.com/1420-3049/28/11/4367/pdf

Reference108 articles.

1. The logic of chemical synthesis: Multistep synthesis of complex carbogenic molecules (nobel lecture);Corey;Angew. Chem. Int. Ed.,1991

2. Carbanions of 1,f Dithianes;Corey;Reagents for C -C Bond Formation by Nucleophilic Displacement and Carbonyl Addition. Angew. Chem. Int. Ed.,1965

3. Generation and synthetic applications of 2-lithio-1,3-dithianes;Seebach;JOC,1975

4. Zur Umpolung der Carbonylreaktivität; Deprotonierung von Ketenthioacetalen zu 1, 1-dithiosubstituierten Allyl-und Pentadienyllithiumverbindungen sowie deren Reaktionen mit Elektrophilen;Seebach;Justus Liebigs Ann. Der Chem.,1977

5. Umpolung of the reactivity of carbonyl compounds through sulfur-containing reagents;Grobel;Synthesis,1977

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