Total synthesis of anti-microtubule diketopiperazine derivatives: phenylahistin and aurantiamine

…, S Orikasa, K Tanaka, K Kanoh, Y Kiso

Index: Hayashi; Orikasa; Tanaka; Kanoh; Kiso Journal of Organic Chemistry, 2000 , vol. 65, # 24 p. 8402 - 8405

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Citation Number: 72

Abstract

The closely related phenylahistin1 1 and aurantiamine2 2 have been isolated from Aspergillus ustus NSC-F038 and Penicillium aurantiogriseum. These diketopiperazine derivatives consist of an L-phenylalanine or L-valine residue, respectively, and a unique isoprenylated dehydrohistidine residue with a quaternary carbon at the 5-position of the imidazole ring. The former is a member of a new class of colchicine-like microtubule ...