Discodermolide Smith total syntheses

Smith, A.B. Ill, Freeze, B.S., Xian, M., Hirose, T. (2005) Total Synthesis of (-l-)-Discodermolide A Highly Convergent Fourth-Generation Approach. Organic Letters, 7, 1825-1828. 

Clinical development is hampered due to the extremely scarce supply of discodermolide from the natural source. Thus, total synthesis provides the only viable route to useful quantities of this novel cytotoxic polyketide. Consequently, there have been considerable synthetic efforts toward the total synthesis of discodermolide [16], Up to date, five total synthesis of (+)- and/or (-)-discodermolide have been reported, one by Schreiber [3], one by Smith [17], one by Myles [18], one by Marshall [19] and one by Paterson [20]. All the syntheses are convergent. Schreiber and Myles employed an analogous connection by using a Nozaki-Kishi addition of a C8 acetylenic or (Z)-vinylic chromium to a C7 aldehyde for the major... 

Smith IIIAB, Freeze BS. (+)-discodermolide total synthesis, construction of novel analogues, and biological evaluation. Tetrahedron 2008 64 261-298. 

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