Total synthesis of (+)-thiazinotrienomycin E.
[formula: see text] The first total synthesis of (+)-thiazinotrienomycin E (1), member of a novel class of cytotoxic ansamycin antibiotics, has been achieved. The synthesis features a highly efficient construction of the aromatic fragment 3 incorporating TBS protection of the aniline, a significantly improved synthesis of (-)-19, an intermediate employed in our trienomycins A and F total syntheses, application of the Kocienski modified Julia protocol to elaborate the E,E,E-triene subunit, an efficient union of 3 and (+)-4, and Mukaiyama macrolactamization to access the thiazinotrienomycin macrolide.
Smith
A B
AB
Department of Chemistry, Monell Chemical Senses Center, University of Pennsylvania, Philadelphia 19104, USA. smithab@sas.upenn.edu
Wan
Z
Z
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013843:Thiazines / Q000138:chemical synthesis
D000900:Anti-Bacterial Agents; D013843:Thiazines; C094829:thiazinotrienomycin E