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油菜甾醇内酯及其类似物的侧链部分合成新方法

Novel Construction of Brassinolide and the Related Compounds' Side Chains
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摘要 以豆甾醇为原料,合成了油菜甾醇内酯及其类似物的侧链部分;并为这一类化合物的侧链部分的合成提供了一条简便、经济、高效的合成方法.其关键步骤为醛5及酮6之间的不对称Aldol反应,以及羰基α位的差向异构化反应. A stereoselective synthesis of brassinolide, which involves construction of the side chain by, highly stereoselective aldol reaction of 205-6beta-methoxy-3alpha,5alpha-cyclo-5alpha-pregnane-20-carboxaldehyde (5) with the anion of alpha-silyloxy ketone 6, is described.
出处 《化学学报》 SCIE CAS CSCD 北大核心 2003年第7期1052-1057,共6页 Acta Chimica Sinica
基金 国家自然科学基金(No.20072012) 高校博士学科专项基金(No.20010730001)
关键词 油菜甾醇内酯 类似物 侧链 合成方法 豆甾醇 植物生长刺激素 brassinolide side chain aldol reaction
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参考文献18

  • 1Grove, M. D.; Spencer, G. F.; Rohwedder, W. K.;Mandava, N.; Worley, J. F. ; Warthen, J. D. Jr. ; Steffens,G. L. ; Flippen-Andetson, J. L. ; Cook, J. C. Jr. Nature 1979,281, 216. 被引量:1
  • 2Adam, G. ; Marquardt, V. Phytochemistry 1986, 25, 1787 and references cited therein. 被引量:1
  • 3Baba, T. Agric. Biol. Chem. 1983, 47, 1409. 被引量:1
  • 4For a recent review of the syntheses of brassinolide, see:Zhou, W. S. ; Zhuang, Z. P. Advances in Steroid Chemistry,Science Press, Beijing, 2002, p.251 (in Chinese) and references cited therein. 被引量:1
  • 5For recent synthetic work on cembranolides using methyl isopropyl ketone and its derivative to found 20-membered carbon chain from this laboratory, see:Li, W. D. Z. ; Li, Y. ; Li, Y. L. Tetrahedron Lett. 1999,40,965. 被引量:1
  • 6For recent synthetic work on cembranolides using methyl isopropyl ketone and its derivative to found 20-membered carbon chain from this laboratory, see:Li, Y. L.; Li, W. D.; Li, Y. J. Chem. Soc., Petkin Trans l 1993, 2953 and references cited therein. 被引量:1
  • 7Anderson, G. D.; Powers, T. J.; Djerasai, C.; Fayos, J.;Clardy, J. J. Am. Chem. Soc. 1975, 97, 388. 被引量:1
  • 8For a recent review of nucleophilic additions to chiral carbonyl compounds, See:Mengel, A. ; Reiser, O. Chem. Rev. 1999, 99, 1191. 被引量:1
  • 9For a recent review of nucleophilic additions to chiral carbonyl compounds,See: The stereochemistry at C-22 is predicted by the Cram or Felin-Anh model for the Transition State. ^1H NMR evidence is in accordance with this since coupling constant between H-22 and H-23 in 22R,23S isomer 15 ( J =3.6 Hz) indicates the preferred conformation for the side chain shown. For the 22R,23R isomer 7 the corresponding couping constant (J = 8.8 Hz) indicates a preferred confrontation for the side chain in which the dihedral angle between H-22 and H-23 is about 180°. 被引量:1
  • 10The migration of TBS group from α-oxygen to β-oxygen is a novel phenomenon in directed aldol reaction. We will describe the phenomenon in detall in a future paper. 被引量:1

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