Solid-Phase Synthesis of Triostin A Using a Symmetrical Bis(diphenylmethyl) Linker System

• Published in: Journal of organic chemistry Vol. 80; no. 15; pp. 7486 - 7494
• Main Authors: Sable, Ganesh A, Lim, Dongyeol
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 07.08.2015; Amer Chemical Soc
• Subjects: amino acids; Chemistry; Chemistry, Organic; Cyclization; depsipeptides; Depsipeptides - chemical synthesis; Depsipeptides - chemistry; diketopiperazines; DNA; DNA - chemistry; organic chemistry; Oxidation-Reduction; Physical Sciences; Quinoxalines - chemical synthesis; Quinoxalines - chemistry; Science & Technology; Solid-Phase Synthesis Techniques; Solutions; Sulfhydryl Compounds - chemistry; synthesis; thiols; ORGANIC-SYNTHESIS; CYCLIC PEPTIDE; SEQUENCE SPECIFICITY; N-TETRAMETHYLTRIOSTIN-A; MARINE MICROMONOSPORA; BIFUNCTIONAL INTERCALATION; BISINTERCALATOR NATURAL-PRODUCTS; QUINOXALINE ANTIBIOTICS; ANTITUMOR-ACTIVITY; PEPTIDE-SYNTHESIS

Triostin A is a symmetric bicyclic depsipeptide with very potent antitumoral activity because of its bisintercalation into DNA. In this study, we report a new synthetic strategy that exploits a structural symmetry of triostin A. First, we prepared a novel symmetric linker molecule that is labile und...