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US 4,374,979 AGranted
Regiospecific synthesis of anthracyclinone compounds such as daunomycinone
AssigneeUniversity of Kansas Endowment Association
InventorLester A. Mitscher
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Abstract
A regiospecific synthesis for anthracyclinones asymmetric is disclosed. The synthesis is based upon a regiospecific bromination of the C-7 position of the .alpha.-tetralone which after transposing the keto group to the .beta.-position and reaction with an organo-lithium compound is condensed with a phthalate ester.
Claims10
A process for synthesizing asymmetric anthracyclinones which comprises:
- (a) brominating a 5,8-dimethoxy-.alpha.-tetralone to yield a 7-bromo-5,8 dimethoxy-.alpha.-tetralone as substantially the only isomer,
- (b) transposing the 1-keto group of said 7-bromo-5,8-dimethoxy-.alpha.-tetralone to the 2-position to yield the corresponding .beta.-tetralone;
- (c) protecting said transposed keto group,
- (d) lithiating said protected .beta.-tetralone,
- (e) reacting said lithiated compound with a phthalate ester, and
- (f) cyclizing said conjugate to yield an anthracyclinone.
3 more elements
Dependencies are inferred from the claim text.