New total synthesis of (+)-cystothiazole A based on palladium-catalyzed cyclization–methoxycarbonylation

K Kato, T Sasaki, H Takayama, H Akita

Index: Kato, Keisuke; Sasaki, Takamitsu; Takayama, Hiroyuki; Akita, Hiroyuki Tetrahedron, 2003 , vol. 59, # 15 p. 2679 - 2685

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Citation Number: 32

Abstract

Palladium-catalyzed cyclization-methoxycarbonylation of (2R, 3S)-3-methylpenta-4-yne-1, 2- diol (6) derived from (2R, 3S)-epoxy butanoate 7 followed by methylation gave the tetrahydro-2-furylidene acetate (−)-10, which was converted to the left-half aldehyde (+)-3. A Wittig reaction between (+)-4 and the phosphoranylide derived from the bithiazole-type phosphonium iodide 4 using lithium bis (trimethylsilyl) amide afforded the (+)- ...