Synthesis of a marine polyether toxin, okadaic acid [4] p1--total synthesis

M Isobe, Y Ichikawa, DL Bai, H Masaki, T Goto

Index: Isobe, Minoru; Ichikawa, Yoshiyasu; Bai, Dong-Lu; Masaki, Hisanori; Goto, Toshio Tetrahedron, 1987 ,  vol. 43,  # 20  p. 4767 - 4776

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Citation Number: 97

Abstract

Three segments A, B and C for okadaic acid synthesis were coupled with each other in the order of A+ (B+ C), the key steps of the twice couplings being between sulfone carbanions and aldehydes. After the B+ C coupling, the asymmetric center C-27 was generated by a hydride reduction of the corresponding ketone 16 under electronic control. The second coupling was followed to form the C-14 15 double bond. Oxidation of the α-oxy aldehyde ...