An approach to versatile intermediates in the synthesis of anthracyclinone aglycone analogs

✍ Scribed by Una O'Connor; William Rosen

• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 241 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)86013-5

✦ Synopsis

Daunorubicin,' adriamycin' and canninomycin3 &a-c) are powerful antitmr anthracyclines having very similar molecular structures. These broad spectrum anticancer agents4 are presently prepared by microbiological fermentation methods but the yields of these reactions are very low thus making these drugs rather inaccessible and costly. 5 The need for a good chemical synthesis is apparent and recently several partial approaches to these problems have appeared. 6 These procedures have exclusively focused on the preparation of the aglycone (anthracyclinone) portion of the molecule, with the synthesis of the sugar (daunosamine) portion' and the coupling8 of this sugar to the aglycone having been accomplished previously.

None of these procedures has been aimed at the preparation of the aglycone analogs and thus we had planned to develop a route that could be used to prepare the parent compounds as well as analogs of these materials.