Efficient total syntheses of (±)protolichesterinic acid and (±)rocellaric acid via tungsten-π-allyl complexes

作者: Ming-Jung Chen , Rai-Shung Liu

DOI: 10.1016/S0040-4039(98)02146-7

关键词:

摘要: Abstract Total syntheses of racemic protolichesterinic acid ( 1 ) and rocellaric 2 were achieved with the use tungsten-π-allyl complex in key step. In this synthetic route, compounds prepared four six steps respectively starting from readily available chloropropargyl derivatives.

参考文章(30)
Lambert Brandsma, Preparative acetylenic chemistry ,(1971)
Johann Mulzer, Nabiollah Salimi, Hans Hartl, First asymmetric synthesis of (+)- and (−)-Roccellaric acid and dihydroprotolichesterinic acid Tetrahedron: Asymmetry. ,vol. 4, pp. 457- 471 ,(1993) , 10.1016/S0957-4166(00)86089-9
Jones reagent, Rosângela de A. Epifanio, Wilson Camargo, Angelo C. Pinto, Oxidative cleavage of 1,2-glycols and α-hydroxy ketones with the ag] Tetrahedron Letters. ,vol. 29, pp. 6403- 6406 ,(1988) , 10.1016/S0040-4039(00)82357-6
J.W. Faller, J.A. John, M.R. Mazzieri, Controlling stereochemistry in crotyl additions to aldehydes with crotylmolybdenum complexes Tetrahedron Letters. ,vol. 30, pp. 1769- 1772 ,(1989) , 10.1016/S0040-4039(00)99575-3
Anna Bernardi, Maria Grazia Beretta, Lino Colombo, Cesare Gennari, Giovanni Poli, Carlo Scolastico, Synthetic opportunities offered by anti .alpha.-methylene-.beta.-hydroxy-.gamma.-alkoxy esters: stereoselective reactions at the double bond Journal of Organic Chemistry. ,vol. 50, pp. 4442- 4447 ,(1985) , 10.1021/JO00223A005
Yoshinori. Yamamoto, Naoki. Asao, SELECTIVE REACTIONS USING ALLYLIC METALS Chemical Reviews. ,vol. 93, pp. 2207- 2293 ,(1993) , 10.1021/CR00022A010
Chi-Chung Chen, Jang-Shyang Fan, Gene-Hsian Lee, Shie-Ming Peng, Sue-Lang Wang, Rai-Shung Liu, Stereochemical Course in Tungsten-Promoted Cyclocarbonylation Reactions To Form Five-, Six-, and Seven-Membered Lactone Rings Journal of the American Chemical Society. ,vol. 117, pp. 2933- 2934 ,(1995) , 10.1021/JA00115A031
Keiko Komori, Hiroyuki Oshita, Yasushi Mizobe, Masanobu Hidai, Preparation and properties of molybdenum and tungsten dinitrogen complexes. 25. Catalytic conversion of molecular nitrogen into silylamines using molybdenum and tungsten dinitrogen complexes Journal of the American Chemical Society. ,vol. 111, pp. 1939- 1940 ,(1989) , 10.1021/JA00187A092