Journal of the American Chemical Society

Total synthesis of (-)-domoic acid. A revision of the original structure

Y Ohfune, M Tomita

Index: Ohfune; Tomita Journal of the American Chemical Society, 1982 , vol. 104, # 12 p. 3511 - 3513

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Citation Number: 218

Abstract

room temperature, 30 min, followed by hydroxyselenati~ nl~ with PhSeC1/THF/Et3N/Hz0, room temperature, 1 h, yielded the a-selenoaldehyde 15* in 90% yield. Several trials to obtain the enal system (cf. 16 and 17, Scheme 111) under usual conditions (30% H202, NaI04, etc.) were not successful. However, oxidative removal of the selenide with O3 (CH2C12,-78" C), followed by trapping of the resultant ben-