Please use this identifier to cite or link to this item: http://hdl.handle.net/2440/86637
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Type: Journal article
Title: A new route to 3-hydroxyphthalides: application to the synthesis of racemic [5-¹³C] daunomycinone
Other Titles: A new route to 3-hydroxyphthalides: application to the synthesis of racemic [5-(13)C] daunomycinone
Author: Becker, A.M.
Irvine, R.W.
McCormick, A.S.
Russell, R.A.
Warrener, R.N.
Citation: Tetrahedron Letters, 1986; 27(29):3431-3434
Publisher: Pergamon Press
Issue Date: 1986
ISSN: 0040-4039
1873-3581
Statement of
Responsibility: 
Anna M. Becker, Robert W. Irvine, Alison S. McCormick, Richard A. Russell, Ronald N. Warrener
Abstract: Lithiation (n-BuLi) of the (3′-methoxyphenyl) oxazoline (2a) occurs specifically at C2′ and, following carboxylation (CO2/13CO2) and esterification, yields the phthalate derivative (e.g.5a). Elaboration of the oxazoline-ring furnishes the related aldehydes which spontaneously cyclise to form the 3-hydroxyphthalides (8/10). The title[5-13C] anthracyclinone (20) is produced from 3-cyanophthalide (11) in good yield and with excellent isotopic efficiency.
Rights: Copyright status unknown
RMID: 0030009213
DOI: 10.1016/S0040-4039(00)84815-7
Appears in Collections:Chemistry publications

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