Tetrahedron

Synthesis of a marine polyether toxin, okadaic acid (2)—synthesis of segment b

Y Ichikawa, M Isobe, T Goto

Index: Ichikawa, Yoshiyasu; Isobe, Minoru; Goto, Toshio Tetrahedron, 1987 ,  vol. 43,  # 20  p. 4749 - 4758

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Citation Number: 46

Abstract

The central synthetic segment B for okadaic acid comprises the carbons from 15 through 27 including 6 asymmetric carbons. Its synthesis started from a D-Glucose derivative, whose carbon was extended twice for the six and five membered etherial ring formation. The original conformation of the sugar was inverted when the spiro-ether was formed to eventuate the axial aldehyde formation in 35 overall steps.