Studies on the Synthesis of Apoptolidin A. 1. Synthesis of the C(1)−C(11) Fragment
作者： Masaki Handa , Karl A. Scheidt , Martin Bossart , Nan Zheng , William R. Roush
DOI: 10.1021/JO702250Z
关键词:
摘要: A synthesis of the C(1)−C(11) fragment apoptolidin has been accomplished by a convergent route involving stereoselective glycosidation 9 and Suzuki cross-coupling reaction bromodienoate 7 vinylborane generated via chemoselective hydroboration diyne 6 with diisopinocampheylborane.
acs.org
sci-hub.se 参考文章(49)
Julia Schuppan, Hermut Wehlan, Sonja Keiper, Ulrich Koert, Apoptolidinone A: synthesis of the apoptolidin A aglycone. Chemistry: A European Journal. ,vol. 12, pp. 7364- 7377 ,(2006) , 10.1002/CHEM.200600461
G.H. Veeneman, S.H. van Leeuwen, J.H. van Boom, Iodonium ion promoted reactions at the anomeric centre. II An efficient thioglycoside mediated approach toward the formation of 1,2-trans linked glycosides and glycosidic esters Tetrahedron Letters. ,vol. 31, pp. 1331- 1334 ,(1990) , 10.1016/S0040-4039(00)88799-7
Akira Kamabuchi, Tsukasa Moriya, Norio Miyaura, Akira Suzuki, Synthesis of Functionalized 1-Alkenylboronates via Hydroboration-Dealkylation of Alkynes with Diisopinocampheylborane Synthetic Communications. ,vol. 23, pp. 2851- 2859 ,(1993) , 10.1080/00397919308012607
Dana M. Gordon, Samuel J. Danishefsky, Displacement reactions of a 1,2-anhydro-α-d-hexopyranose: installation of useful functionality at the anomeric carbon Carbohydrate Research. ,vol. 206, pp. 361- 366 ,(1990) , 10.1016/0008-6215(90)80075-E
Norio. Miyaura, Akira. Suzuki, Palladium-catalyzed cross-coupling reactions of organoboron compounds Chemical Reviews. ,vol. 95, pp. 2457- 2483 ,(1995) , 10.1021/CR00039A007
Noriyuki Nakajima, Kiyoshi Horita, Reiko Abe, Osamu Yonemitsu, MPM (4-methoxybenzyl) protection of hydroxy functions under mild acidic conditions Tetrahedron Letters. ,vol. 29, pp. 4139- 4142 ,(1988) , 10.1016/S0040-4039(00)80438-4
Robert W. Murray, Ramasubbu Jeyaraman, Dioxiranes: synthesis and reactions of methyldioxiranes Journal of Organic Chemistry. ,vol. 50, pp. 2847- 2853 ,(1985) , 10.1021/JO00216A007
Robert E. Ireland, Longbin Liu, An improved procedure for the preparation of the Dess-Martin periodinane Journal of Organic Chemistry. ,vol. 58, pp. 2899- 2899 ,(1993) , 10.1021/JO00062A040
Bernd Renneberg, Yue-Ming Li, Hartmut Laatsch, Heinz-Herbert Fiebig, A short and efficient transformation of rhamnose into activated daunosamine, acosamine, ristosamine and epi-daunosamine derivatives, and synthesis of an anthracycline antibiotic acosaminyl-ε-iso-rhodomycinone Carbohydrate Research. ,vol. 329, pp. 861- 872 ,(2000) , 10.1016/S0008-6215(00)00257-3
K. C. Nicolaou, Konstantina C. Fylaktakidou, Holger Monenschein, Yiwei Li, Bernd Weyershausen, Helen J. Mitchell, Heng-xu Wei, Prasuna Guntupalli, David Hepworth, Kazuyuki Sugita, Total synthesis of apoptolidin: construction of enantiomerically pure fragments. Journal of the American Chemical Society. ,vol. 125, pp. 15433- 15442 ,(2003) , 10.1021/JA0304953