Jiménez, M and Zhu, W and Vogt, A and Day, BW and Curran, DP
(2011)
Efficient syntheses of 25,26-dihydrodictyostatin and 25,26-dihydro-6-epi- dictyostatin, two potent new microtubule-stabilizing agents.
Beilstein Journal of Organic Chemistry, 7.
1372 - 1378.
ISSN 1860-5397
Abstract
The dictyostatins are powerful microtubule-stabilizing agents that have shown antiproliferative activity against a variety of human cancer cell lines. Two highly active analogs of dictyostatin, 25,26-dihydrodictyostatin and 25,26-dihydro-6-epi-dictyostatin, were prepared by a new streamlined total synthesis route. Three complete carbon fragments were prepared to achieve maximum convergency. These were coupled by a Horner-Wadsworth-Emmons reaction sequence and an esterification. A late stage Nozaki-Hiyama-Kishi reaction was then used to form the 22-membered macrolide. The stereoselectivity of this reaction depended on the configurations of the nearby stereocenter at C6. © 2011 Verma et al; licensee Beilstein-Institut.
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