The Journal of Organic Chemistry

Synthesis of verrucarin B

WR Roush, TA Blizzard

Index: Roush, William R.; Blizzard, Timothy A. Journal of Organic Chemistry, 1984 , vol. 49, # 23 p. 4332 - 4339

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Citation Number: 66

Abstract

A four-step synthesis of verrucarin B (3) from verrucarol (2) is described. Coupling of 2 with in situ generated carboxylic acid 5 proceeded with moderate regioselectivity and afforded trichothecene monoester 14 in only 35% yield. It was necessary therefore to block the C (4)- hydroxyl group of verrucarol prior to the coupling reaction with 5. Selective protection of 2 was accomplished in 54% yield (81% corrected for recovered verrucarol after hydrolysis of ...