Biologically active quassinoids : synthetic methodology for the conversion of chaparrin into glaucarubolone esters and quassinoid analogs1 1 For previous paper in this series see: C. Moretti, S. Bhatnagar, J.C. Beloeil and J. Polonsky, J. Nat. Prods., 49, 440 (1986)
Biologically inactive but easily available chaparrin 2a has been converted into potent antileukemic C-15 esters of glaucarubolone 2b and quassinoid analogs in which the C-15 ester side chain has been replaced by an alkyl or alkenyl group.The synthetic methodology developed has been applied to the preparation of C-15 ester derivatives 15, 16, 17 and quassinoid analogs 12, 13 and 14.
Bhatnagar, Subodh C.,Caruso, Andrew J.,Polonsky, Judith,Rodriguez, Berta Soto
p. 3471 - 3480
(2007/10/02)
SYNTHETIC STUDIES IN THE QUASSINOID SERIES. CONVERSION OF CHAPARRIN INTO CASTELANONE AND QUASSINOID ANALOGS.
Inactive chaparrin 1 has been converted in seven steps and 16 percent overall yield to castelanone 3 which is known to inhibit significantly growth of the murine lymphocytic leukemia P-388 cell line.The methodology developed has been applied to the preparation of quassinoid analogs 15, 16 and 17.
Caruso, Andrew J.,Polonsky, Judith,Rodriguez, Bertha Soto
p. 2567 - 2570
(2007/10/02)
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