Total synthesis of mycothiazole, a polyketide heterocycle from marine sponges

✍ Scribed by Hideyuki Sugiyama; Fumiaki Yokokawa; Takayuki Shioiri

• Book ID: 104205606
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 427 KB
• Volume: 59
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(03)01020-2

✦ Synopsis

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).