Tetrahedron letters

A new route to 3-hydroxyphthalides: Application to the synthesis of racemic [5-13C] daunomycinone.

…, RW Irvine, AS McCormick, RA Russell, RN Warrener

Index: Becker, Anna M.; Irvine, Robert W.; McCormick, Alison S.; Russell, Richard A.; Warrener, Ronald N. Tetrahedron Letters, 1986 ,  vol. 27,  # 29  p. 3431 - 3434

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Citation Number: 9

Abstract

Abstract Lithiation (n-BuLi) of the (3′-methoxyphenyl) oxazoline (2a) occurs specifically at C2′ and, following carboxylation (CO 2/13 CO 2) and esterification, yields the phthalate derivative (eg 5a). Elaboration of the oxazoline-ring furnishes the related aldehydes which spontaneously cyclise to form the 3-hydroxyphthalides (8/10). The title [5-13 C] anthracyclinone (20) is produced from 3-cyanophthalide (11) in good yield and with ...