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Total Synthesis of (−)-Epothilone A

✍ Scribed by Prof. Dr. Dieter Schinzer; Dipl.-Chem. Anja Limberg; Dipl.-Chem. Armin Bauer; Dipl.-Chem. Oliver M. Böhm; Dr. Martin Cordes

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
231 KB
Volume
36
Category
Article
ISSN
0044-8249

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✦ Synopsis

  1. !L = 10.11 cm-I. crystal dimensions 0.3 x 0 3x0.4mm. Mo,, radiation (0.71073 A). measurement at 150(2) K. Final R (on F) and wR2 (on F2) were 0 030 and 0 090. respectively, for all 11 760 unique data. Final G O F = 0.95. and the final difference fourier map showed no peak at greater than + 0.891 and less than -0.629 e k 3 . A Flack i parameter of -0.009(8) showed the refinement had been carried out with the correct polarity. 3: C,,H,,DyF,N,,O,,S,.

M , = 1570 9X. orthorhombic. space group P 2 , 2 , 2 , , u = 15 7679(4). h = 20.3133(4). ( = 21.7304(4) A, U = 6960.2(3) A'. 2 = 4, pCorr = 1.499 gcm-3. F(000) = 3216. p = 12 55 cm-'. crystal dimensions 0.2 x 0.3 x 0.3 mm. Ma,, radiation (1).71073 A). measurement at 150(2)K Final R (on F ) and 1rR2 (on F 2 ) were 0.042 and 0.1174, respectively, for all 12017 unique data. Final GOF = 1.097. and the final difference fourier map showed no peak at greater than f0.993 and less than -1.088 e k ' . A Flack Y parameter of -0.02119) showed the refinement had been carried out with the correct polarity. Crystal

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The formal total synthesis of epothilone A is described. The 3 is formed by introduction of the thiazole moiety by a Wittig reaction and subsequent functional group transformation. An key steps in the synthesis of the northern hemisphere are a Z-selective ten-membered ring-closing metathesis reactio