e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521
Total syntheses of epothilones A and B via a macrolactonization-based strategy
…, S Ninkovic, F Sarabia, D Vourloumis…
Index: Nicolaou; Ninkovic; Sarabia; Vourloumis; He; Vallberg; Finlay; Yang Journal of the American Chemical Society, 1997 , vol. 119, # 34 p. 7974 - 7991
The total syntheses of epothilones A (1) and B (2) and several analogues thereof are described. The reported strategy relies on a macrolactonization approach and features selective epoxidation of the macrocycle double bond in precursors 3 and 4 (Scheme 1), respectively, as well as high convergency and flexibility. Building blocks 9-12 and 15 were constructed by asymmetric processes and coupled via Wittig, aldol, and ...
[Keck, Gary E.; Giles, Robert L.; Cee, Victor J.; Wager, Carrie A.; Yu, Tao; Kraft, Matthew B. Journal of Organic Chemistry, 2008 , vol. 73, # 24 p. 9675 - 9691]
[Dongfang, Meng; Bertinato, Peter; Balog, Aaron; Su, Dai-Shi; Kamenecka, Ted; et al. Journal of the American Chemical Society, 1997 , vol. 119, # 42 p. 10073 - 10092]
![(5S)-6-[tert-butyl(dimethyl)silyl]oxy-5-methylhexanal Structure](https://image.chemsrc.com/caspic/454/190369-75-6.png)
![(3S,7S,8S,12Z,15S,16E)-3,7,15-tris[[tert-butyl(dimethyl)silyl]oxy]-1-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one Structure](https://image.chemsrc.com/caspic/459/193146-53-1.png)
![(5S)-5-{[(tert-butyl)dimethylsilyl]oxy}-7-hydroxy-4,4-dimethylheptan-3-one Structure](https://image.chemsrc.com/caspic/004/250679-53-9.png)
(3Z)-4-methylhepta-3,6-dienyloxy}-1,1,2,2-tetramethyl-1-silapropane Structure](https://image.chemsrc.com/caspic/176/193146-43-9.png)
![(3S,7S,8S,12Z,15S,16E)-3,7,15-tris[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid Structure](https://image.chemsrc.com/caspic/252/193146-63-3.png)
![(3S,7S,8S,12Z,15S,16E)-1,3,15-tris[[tert-butyl(dimethyl)silyl]oxy]-7-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one Structure](https://image.chemsrc.com/caspic/438/193146-49-5.png)
![(3S,7S,8S,12Z,15S,16E)-1,3,7,15-tetrakis[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one Structure](https://image.chemsrc.com/caspic/045/193146-51-9.png)
![(5S)-5,7-Bis-{[tert-butyldimethylsilyl)oxy]}-4,4-dimethylheptan-3-one Structure](https://image.chemsrc.com/caspic/298/187527-25-9.png)
![(3S,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-al Structure](https://image.chemsrc.com/caspic/132/188730-08-7.png)
