Total synthesis of the natural HDAC inhibitor Cyl-1. Issue 18 (24th April 2018)

• Record Type: Journal Article
• Authors: Servatius, Phil; Kazmaier, Uli
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 18(2018)
• Page Start: 3464
• Page End: 3472
• Publication Date: 2018-04-24
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob00391b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A chelate enolate Claisen rearrangement was used as a key step in the first total synthesis ofCyl-1, a cyclic tetrapeptide from Cylindrocladium scoparium . Abstract : Chelate enolate Claisen rearrangements are powerful reactions for constructing amino acid scaffolds. They generally proceed via chair-like transition states with excellent transfer of stereogenic information. Utilizing this reaction in natural product synthesis gives access to non-proteinogenic amino acids such as (2 S, 9 S )-2-amino-8-oxo-9, 10-epoxydecanoic acid (Aoe), the unusual amino acid of a series of histone deacetylase inhibitors (HDACi). Herein the first total synthesis ofCyl-1, a cyclotetrapeptide from Cylindrocladium scoparium, is described.