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

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dc.contributor.authorBecker, A.M.
dc.contributor.authorIrvine, R.W.
dc.contributor.authorMcCormick, A.S.
dc.contributor.authorRussell, R.A.
dc.contributor.authorWarrener, R.N.
dc.date.issued1986
dc.description.abstractLithiation (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.
dc.description.statementofresponsibilityAnna M. Becker, Robert W. Irvine, Alison S. McCormick, Richard A. Russell, Ronald N. Warrener
dc.identifier.citationTetrahedron Letters, 1986; 27(29):3431-3434
dc.identifier.doi10.1016/S0040-4039(00)84815-7
dc.identifier.issn0040-4039
dc.identifier.issn1873-3581
dc.identifier.urihttp://hdl.handle.net/2440/86637
dc.language.isoen
dc.publisherPergamon Press
dc.rightsCopyright status unknown
dc.source.urihttps://doi.org/10.1016/s0040-4039(00)84815-7
dc.titleA new route to 3-hydroxyphthalides: application to the synthesis of racemic [5-¹³C] daunomycinone
dc.title.alternativeA new route to 3-hydroxyphthalides: application to the synthesis of racemic [5-(13)C] daunomycinone
dc.typeJournal article
pubs.publication-statusPublished

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