Total synthesis of (+)-laurencin
作者： Kazunori Tsushima , Akio Murai
DOI: 10.1016/S0040-4039(00)74256-0
关键词: Lactone 、 Metabolite 、 Organic chemistry 、 Cyclic ether 、 Chemistry 、 Total synthesis 、 Natural product 、 Red algae 、 Enantiomer
摘要: Abstract The first total synthesis of (+)-laurencin (1), which is the most representative marine natural product isolated from red algae, described via intermediates 2–18. Key steps in include a facile oxidative preparation 2, an effective conversion 9a to 11, and SmI2-catalyzed elongation reaction 15, providing 16a.
elsevier.com
sci-hub.se 参考文章(18)
K. Mori, T. Takigawa, T. Matsuo, Synthesis of optically active forms of ipsdienol and ipsenol : The pheromone components of ips bark beetles Tetrahedron. ,vol. 35, pp. 933- 940 ,(1979) , 10.1016/S0040-4020(01)93705-6
J.Stephen Clark, Andrew B. Holmes, A strategy for the asymmetric synthesis of medium ring oxygen heterocycles: Enantioselective total synthesis of (+)-octahydrodeacetyldebromolaurencin Tetrahedron Letters. ,vol. 29, pp. 4333- 4336 ,(1988) , 10.1016/S0040-4039(00)80490-6
K. C. Nicolaou, D. G. McGarry, P. K. Somers, B. H. Kim, W. W. Ogilvie, G. Yiannikouros, C. V. C. Prasad, C. A. Veale, R. R. Hark, Synthesis of medium-sized ring ethers from thionolactones. Applications to polyether synthesis Journal of the American Chemical Society. ,vol. 112, pp. 6263- 6276 ,(1990) , 10.1021/JA00173A013
Leo A. Paquette, Thomas J. Sweeney, A concise total synthesis of enantiomerically pure (+)-cis- and (+)-trans-lauthisan Journal of Organic Chemistry. ,vol. 55, pp. 1703- 1704 ,(1990) , 10.1021/JO00293A006
K. C. Nicolaou, D. G. McGarry, P. K. Somers, C. A. Veale, G. T. Furst, Nucleophilic additions to thionolactones. New synthetic technology for the construction of medium and large ring ethers Journal of the American Chemical Society. ,vol. 109, pp. 2504- 2506 ,(1987) , 10.1021/JA00242A041
Tadashi Masamune, Hajime Matsue, Hisashi Murase, Synthetic Studies of Laurencin and Related Compounds. IV. Synthesis ofcis-2-Ethyl-8-formyl-3,4,7,8-dihydro-2H-oxocin-3-one 3-Ethylene Acetal and Related Compounds Bulletin of the Chemical Society of Japan. ,vol. 52, pp. 127- 134 ,(1979) , 10.1246/BCSJ.52.127
Tadashi Masamune, Hisashi Murase, Hajime Matsue, Akio Murai, Synthetic Studies of Laurencin and Related Compounds. V. Transformation ofcis-2-Ethyl-8-formyl-3,4,7,8-dihydro-2H-oxocin-3-one 3-Ethylene Acetal into (±)-Laurencin Bulletin of the Chemical Society of Japan. ,vol. 52, pp. 135- 141 ,(1979) , 10.1246/BCSJ.52.135
J. Souppe, J.L. Namy, H.B. Kagan, Samarium diiodide as coupling agent between aldehydes and organic halides for the synthesis of homoallylic and homobenzylic alcohols Tetrahedron Letters. ,vol. 23, pp. 3497- 3500 ,(1982) , 10.1016/S0040-4039(00)87651-0
T. Irie, M. Suzuki, T. Masamune, Laurencin, a constituent of Laurencia glandulifera Kutzing Tetrahedron. ,vol. 24, pp. 4193- 4205 ,(1968) , 10.1016/0040-4020(68)88180-3
Toshi Irie, Minoru Suzuki, Tadashi Masamune, Laurencin, a constituent from species Tetrahedron Letters. ,vol. 6, pp. 1091- 1099 ,(1965) , 10.1016/S0040-4039(00)90038-8