Efficient Solid-Phase-Based Total Synthesis of the Bisintercalator TANDEM

• Published in: Journal of organic chemistry Vol. 70; no. 19; pp. 7654 - 7661
• Main Authors: Malkinson, John P, Anim, Michael K, Zloh, Mire, Searcey, Mark, Hampshire, Andrew J, Fox, Keith R
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 16.09.2005; Amer Chemical Soc
• Subjects: Anti-Bacterial Agents - chemical synthesis; Chemistry; Chemistry, Organic; DNA - metabolism; Exact sciences and technology; Organic chemistry; Peptides; Physical Sciences; Preparations and properties; Quinoxalines - chemical synthesis; Quinoxalines - metabolism; Science & Technology; HYDROXYL-GROUPS; TRIOSTIN-A; AMINO-ACIDS; DNA; N-TETRAMETHYLTRIOSTIN-A; SEQUENCE PREFERENCES; COLOR TEST; QUINOXALINE ANTIBIOTICS; PEPTIDE-SYNTHESIS; BINDING-SITES; Organic disulfide; Cyclization; Peptides; Structure activity relation; Depsipeptide; Nitrogen heterocycle; Analog; Lactam; Solid phase; Total synthesis; Chromophore

In this article, the first solid-phase-based total synthesis of TANDEM, a synthetic analogue of triostin A, is described. In initial studies, the synthesis incorporated depsipeptide formation, introduction of chromophores, and disulfide bond formation on the solid phase, prior to a final solution-ph...