Synthesis and Chemistry of Quinone Methide Models for the Anthracycline Antitumor Antibiotics
The Journal of Organic Chemistry1997Vol. 62(17), pp. 5884–5892
Citations Over TimeTop 15% of 1997 papers
Abstract
In an effort to further understand the chemistry of anthracycline-type quinone methides, two tetracyclic o-quinone methides, 4,5,12-trimethoxy-11-[(trimethylacetyl)oxy]-9,10-dihydro-6(2H)-naphthacenone (19) and (±)-9-carbomethoxy-4,5,12-trimethoxy-11-[(trimethylacetyl)oxy]-9,10-dihydro-6(2H)-naphthacenone (20), were synthesized, and their reaction with several nucleophiles was investigated. Carbon- and sulfur-based nucleophiles afforded stable adducts while oxygen- and nitrogen-based nucleophiles afforded unstable adducts due to the reversibility of the addition. Adducts of 19 with ethanol and O-silylated adenosine (27) were acetylated to afford stable phenol acetates 21 and 29, respectively.
Related Papers
- → ortho-Quinone Methides from para-Quinones: Total Synthesis of Rubioncolin B(2008)125 cited
- → Structure−Activity Study on the Quinone/Quinone Methide Chemistry of Flavonoids(2001)157 cited
- → Nonenzymatic transformations of enzymatically generated N‐acetyldopamine quinone and isomeric dihydrocaffeiyl methyl amide quinone(1989)22 cited
- → Mechanism of activation of 1,2‐dehydro‐N‐acetyldopamine for cuticular sclerotization(1990)20 cited
- → On the mechanism of side chain oxidation of N‐β‐alanyldopamine by cuticular enzymes from Sarcophaga bullata(1990)18 cited