Total synthesis of complex 2,5-diketopiperazine alkaloids

Katherine L Walker; Richard P Loach; Mohammad Movassaghi

doi:10.1016/bs.alkal.2023.06.002

Total synthesis of complex 2,5-diketopiperazine alkaloids

Alkaloids Chem Biol. 2023:90:159-206. doi: 10.1016/bs.alkal.2023.06.002. Epub 2023 Aug 7.

Authors

Katherine L Walker¹, Richard P Loach¹, Mohammad Movassaghi²

Affiliations

¹ Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA, United States.
² Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA, United States. Electronic address: movassag@mit.edu.

PMID: 37716796
PMCID: PMC10955524 (available on 2024-08-07)
DOI: 10.1016/bs.alkal.2023.06.002

Abstract

The 2,5-diketopiperazine (DKP) motif is present in many biologically relevant, complex natural products. The cyclodipeptide substructure offers structural rigidity and stability to proteolysis that makes these compounds promising candidates for medical applications. Due to their fascinating molecular architecture, synthetic organic chemists have focused significant effort on the total synthesis of these compounds. This review covers many such efforts on the total synthesis of DKP containing complex alkaloid natural products.

Keywords: Alkaloid; Cyclodipeptide; Diketopiperazine; Natural product; Synthesis.

Publication types

Review

MeSH terms

Alkaloids*
Biological Products*
Diketopiperazines / pharmacology
Proteolysis

Substances

2,5-dioxopiperazine
Diketopiperazines
Alkaloids
Biological Products

Abstract

Publication types

MeSH terms

Substances

Grants and funding