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Anthracyclinones VI. Diastereoselective synthesis of 7,10-dihydroxy-4-demethoxy-anthracyclinones

✍ Scribed by Emmanuel Bertounesque; Jean-Claude Florent; Claude Monneret

Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 289 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)97265-4

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✦ Synopsis

The total synthesis of two new enantiomerically pure anthracyclinones 9 and 10 from leucoquinizarin 2 and chiral aldehyde 3 readily obtained from a-D-isosaccharinolactone. is described. The stereochemical results are discussed.

We have previously reported 2 an efficient synthesis of 1 from leucoquinizarin 2 and the chiral aldehyde 3 in which the initial C-C bond was formed by an intermolecular Marschalk or Lewis4 reaction and the second one by an intramolecular Marschalk condensation.

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