| Autor: |
Andrus MB; Brigham Young University, Department of Chemistry and Biochemistry, C100 BNSN, Provo, UT 84602-5700, USA. mbandrus@chemdept.byu.edu, Meredith EL, Simmons BL, Soma Sekhar BB, Hicken EJ |
| Jazyk: |
angličtina |
| Zdroj: |
Organic letters [Org Lett] 2002 Oct 03; Vol. 4 (20), pp. 3549-52. |
| DOI: |
10.1021/ol0267432 |
| Abstrakt: |
Geldanamycin (GA), an antitumor Hsp90 inhibitor, was made for the first time by using an oxidative demethylation reaction as the final step. A biaryldioxanone auxiliary set the anti C11-12 hydroxy-methoxy functionality and a methylglycolate auxiliary based on norephedrine was used for the syn C6-7 methoxy-urethane. p-Quinone-forming oxidants, CAN and AgO, produced an unusual aza-quinone product. Nitric acid gave GA from a trimethoxy precursor in 55% yield as a 1:10 mixture with nonnatural o-quino-GA. [structure: see text] |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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