New total synthesis of (+)-cystothiazole A

✍ Scribed by Keisuke Kato; Akira Nishimura; Yasuhiro Yamamoto; Hiroyuki Akita

• Book ID: 104232248
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 66 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)02207-9

✦ Synopsis

Palladium-catalyzed cyclization-methoxycarbonylation of (2R,3S)-3-methylpenta-4-yne-1,2-diol (7) derived from (2R,3S)-epoxy butanoate 8 followed by methylation gave the tetrahydro-2-furylidene acetate (-)-9, which was converted to the left-half aldehyde (+)-4. A Wittig reaction between (+)-4 and the phosphoranylide derived from the bithiazole-type phosphonium iodide 5 using lithium bis(trimethylsilyl)amide afforded the (+)-cystothiazole A (2).