Application of hitherto unexplored macrocyclization strategies in the epothilone series: novel epothilone analogs by total synthesis
作者： Jon T. Njardarson , Kaustav Biswas , Samuel J. Danishefsky
DOI: 10.1039/B209941A
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摘要: A total synthesis of Epothilone 490 and a 11-hydroxy dEpoB utilizing vinyl-boronate cross-metathesis followed by Suzuki macrocyclization. mild route to reach aldehydes from terminal olefins, anticipating Nozaki–Kishi macrocyclization is described.
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Helen E. Blackwell, Daniel J. O'Leary, Arnab K. Chatterjee, Rebecca A. Washenfelder, D. Andrew Bussmann, Robert H. Grubbs, New Approaches to Olefin Cross-Metathesis Journal of the American Chemical Society. ,vol. 122, pp. 58- 71 ,(2000) , 10.1021/JA993063U
David M. Hodgson, Lee T. Boulton, Graham N. Maw, Chemoselectivity in the chromium(II)-mediated synthesis of E-alkenylstannanes from aldehydes and Bu3SnCHBr2 Tetrahedron Letters. ,vol. 35, pp. 2231- 2234 ,(1994) , 10.1016/S0040-4039(00)76805-5
G Oddon, D Uguen, Total synthesis of an aglycone of spiramycin Tetrahedron Letters. ,vol. 39, pp. 1157- 1160 ,(1998) , 10.1016/S0040-4039(97)10758-4
JoséM. Seco, Shamyl K. Latypov, Emilio Quiñoá, Ricardo Riguera, Determining factors in the assignment of the absolute configuration of alcohols by NMR. The use of anisotropic effects on remote positions Tetrahedron. ,vol. 53, pp. 8541- 8564 ,(1997) , 10.1016/S0040-4020(97)00512-7
K. Takai, M. Tagashira, T. Kuroda, K. Oshima, K. Utimoto, H. Nozaki, Reactions of alkenylchromium reagents prepared from alkenyl trifluoromethanesulfonates (triflates) with chromium(II) chloride under nickel catalysis Journal of the American Chemical Society. ,vol. 108, pp. 6048- 6050 ,(1986) , 10.1021/JA00279A068
Robert H. Grubbs, Scott J. Miller, Gregory C. Fu, Ring-Closing Metathesis and Related Processes in Organic Synthesis Accounts of Chemical Research. ,vol. 28, pp. 446- 452 ,(1995) , 10.1021/AR00059A002
James D. White, Roger Hanselmann, Randy W. Jackson, Warren J. Porter, Yoshihiro Ohba, Thomas Tiller, Shan Wang, Total synthesis of rutamycin B, a macrolide antibiotic from Streptomyces aureofaciens. Journal of Organic Chemistry. ,vol. 66, pp. 5217- 5231 ,(2001) , 10.1021/JO0104429
Haolun. Jin, Junichi. Uenishi, William J. Christ, Yoshito. Kishi, Catalytic effect of nickel(II) chloride and palladium(II) acetate on chromium(II)-mediated coupling reaction of iodo olefins with aldehydes Journal of the American Chemical Society. ,vol. 108, pp. 5644- 5646 ,(1986) , 10.1021/JA00278A057
Kaustav Biswas, Hong Lin, Jon T. Njardarson, Mark D. Chappell, Ting-Chao Chou, Yongbiao Guan, William P. Tong, Lifeng He, Susan B. Horwitz, Samuel J. Danishefsky, Highly concise routes to epothilones: the total synthesis and evaluation of epothilone 490. Journal of the American Chemical Society. ,vol. 124, pp. 9825- 9832 ,(2002) , 10.1021/JA0262333
Alois Fürstner, Carbon−Carbon Bond Formations Involving Organochromium(III) Reagents Chemical Reviews. ,vol. 99, pp. 991- 1045 ,(1999) , 10.1021/CR9703360