Adelaide Research & Scholarship
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https://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: the international journal for the rapid publication of all preliminary communications in organic chemistry, 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 |
| DOI: | 10.1016/S0040-4039(00)84815-7 |
| Published version: | http://dx.doi.org/10.1016/s0040-4039(00)84815-7 |
| Appears in Collections: | Aurora harvest 2 Chemistry publications |
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