292073-47-3

Upstream product

• 82994-41-0 (E)-3-(tri-n-butylstannyl)-2-propen-1-ol 
• 292073-43-9 4-bromomethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole 
• 14002-80-3 Methyl 2,2-dimethyl-3-hydroxypropionate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 147509-22-6 3-((tert-butyldiphenylsilyl)oxy)-2,2-dimethylpropan-1-ol 
• 292073-45-1 methyl 2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazolidine-4-carboxylate 
• 292073-46-2 methyl 2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazol-4-carboxylate 
• 292073-56-4 4-hydroxymethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole 
• 292073-50-8 methyl 3-((tert-butyl(diphenyl)silyl)oxy)-2,2-dimethylpropanoate 

Downstream Products

• 292073-49-5 (E)-2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]-4-(hexa-2,5-dienyl)thiazole 
• 292073-48-4 4-((2E)-4-bromobut-2-enyl)-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazole 

Relevant academic research and scientific papers

Total synthesis of mycothiazole, a polyketide heterocycle from marine sponges

Mycothiazole isolated from marine sponges has been efficiently synthesized in a convergent manner. The key reactions involve the thiazole synthesis by dehydrogenation of the thiazolidine with chemical manganese dioxide (CMD), the Stille coupling, and the Nagao asymmetric acetate aldol reaction using the chiral 1,3-thiazolidine-2-thione. This synthesis clearly established the absolute configuration of natural mycothiazole to be (R).

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 re