Asymmetric total synthesis of (-)-mycothiazole.
[structure: see text] In this Letter we describe the first total synthesis of mycothiazole, a polyketide thiazole from a marine sponge. Key steps include our CMD oxidation for the conversion of thiazolidine 11 to thiazole 12 and the Nagao acetate aldol reaction of 5 with aldehyde 4 to construct the chiral secondary alcohol. The skipped diene was constructed by the standard Stille coupling, and the conjugated diene was synthesized by lithium(I)- and copper(I)-mediated Stille coupling.
Sugiyama
H
H
Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan.
Yokokawa
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F
Shioiri
T
T
D000818:Animals; D006900:Hydroxylation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011161:Porifera / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013844:Thiazoles / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D013844:Thiazoles