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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 20, Number 5
BKCSDE 20(5)
May 20, 1999 

Synthesis of 11-Deoxydaunomycinone and Novel 10-Fluoroanthracyclinone Derivatives
Young S. Rho, Younghee Choi, Gyuil Kim, Hongsig Sin, Dong Jin Yoo, Sun-Ha Kim, Chaejoon Cheong
11-Deoxydaunomycinone 15 and 10-fluoroanthracyclinone derivatives 9, 10 were obtained. Naphthalenone 4 prepared from 2-(2,4-pentadienyl)-1,3-dioxane 2 with methyl vinyl ketone and hydrolysis with HClO4 was condensed with phthalidesulfone 5 through Michael type reaction, and was converted to 7 by epoxidation. Epoxide 7 was transformed to trione 12 using reduction-oxidation or hydrofluorination process, and then to 15 by introducing several functional groups. Compound 8 obtained in the course of the reaction of epoxide 7 and HF/ Pyr was used for the synthesis of compounds 9, 10.
551 - 555
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