Studies on the Model Synthesis of the Brassinolide and Dolicholide Side Chains

Studies on the Model Synthesis of the Brassinolide and Dolicholide Side Chains

下载PDF

导出

摘要 A stereoselective synthesis of brassinolide and dolicholide, which involves construction of the side chain enantiomers by a highly stereoselective aldol reaction of aldehyde 5 with the anion of α-silyloxy ketone 6 is described. A stereoselective synthesis of brassinolide and dolicholide, which involves construction of the side chain enantiomers by a highly stereoselective aldol reaction of aldehyde 5 with the anion of α-silyloxy ketone 6 is described.

作者 Li Zeng PENG, Feng Zhi ZHANG, Tian Sheng MEI, Yu Lin LINational Laboratory of Applied Organic Chemistry, Institute of Organic Chemistry, Lanzhou University, Lanzhou 730000

出处《Chinese Chemical Letters》 SCIE CAS CSCD 2003年第9期889-892,共4页 中国化学快报（英文版）

基金 supported by the National Natural Science Foundation of China(Grant No.20072012) the Special Research Grant for Doctoral Sites in Chinese Universities(Grant No.20010730001).

关键词 BRASSINOLIDE dolicholide side chain aldol reaction. Brassinolide, dolicholide, side chain, aldol reaction.

分类号 O621 [理学—有机化学]

引文网络
相关文献

参考文献9

1M. D. Grove. G. F. Spence. W. K. Rohwedder. et al.. Nature. 1979. 281, 216.
2G. Adam, V. Marquardt, Phytochemistry, 1986, 25, 1787, and references cited therein.
3For a recent review of the syntheses of brassinolide, see: Advances in Steroid Chemistry, W.S. Zhou, Z. P. Zhuang, Science Press, Beijing. 2002.251 and references cited therein.
4W. D. Z. Li, Y. Li, Y.L. Li, Tetrahedron Lett.1999, 40. 965 and references cited therein.
5N. Nakajima, K. Horita, R. Abe, et al., Tetrahedron Lett., 1988, 29, 4139.
6(a) For the recent review of nucleophilic additions to chiral carbonyl compounds, see: A.Mengel, O. Reiser, Chem. Rev. 1999, 99, 1191. (b) The stereochemistry at C-3 is predicted by the Cram or Felin-Anh model for the transition state. According to the 1HNMR data, the preferred conformation of ismer 14 is 3S, 4S. Since the coupling constant of H-3 and H-4 is 3.6 Hz. While the preferred comformation of isomer 8 is 3S,4R. The J value of H-3 and H-4 is 8.8 Hz, the dihehral angle between H-3 and H-4 is about 1 80°.
7For a recent review of Mukaiyama aldol reaction, see: R. Mahrwald, Chem. Rev. 1999, 99,1095.
8(a) S. K. Kwan, D. H. Sung, Tetrahedron Lett., 2000, 41, 5909. (b) The corresponding TMS and TBS enol ethers are stable enough to be purified by flash column chromatography on SiO2. (c) The geometry of silyl enol ethers 15 was deduced as Z by 1H NMR and GC (> 98%) analysis and comoared with literature^8a.
9For examples, see: (a) P. A. Lee, V. S. Martin, S. Masamume, et al., J. Am. Chem. Soc., 1982,104, 3515. (b) A. W. M. Lee, Magnetic Resonance in Chemistry. 1985. 23.468.

1彭立增,张逢质,梅天胜,张涛,刘华伟,李裕林.Studies on the Model Synthesis of the Brassinolide and Dolicholide's Side Chains[J].Chinese Journal of Chemistry,2003,21(7):893-897.
2朱洁,包敬广,童雅敏.Brassinolide类物质的合成[J].云南化工,2000,27(4):25-27.
3周维善,戈传生.A NOVEL METHOD FOR CONSTRUCTION OF SIDE CHAIN OF BRASSINOSTEROIDS[J].Science China Chemistry,1989,32(11):1290-1299.
4王成章,沈兆邦,陈祥.银杏叶聚戊烯醇化学研究[J].林产化学与工业,1992,12(4):279-286. 被引量：35
5Wei Shan ZHOU,Li Qiang SUN,Xin Fu PAN.STUDIES ON STEROIDAL PLANT GROWTH REGULATOR 24. STEREOCONTROLLED CONSTRUCTION OF THE SIDE CHAIN OF BRASSINOLIDE AND HOMOBRASSINOLIDE VIA A TANDEM VICINAL DIALKYLATION OF PYRANONE MOIETY[J].Chinese Chemical Letters,1991,2(12):929-932. 被引量：1
6六边变五边,科学家模拟合成新型石墨烯[J].炭素技术,2015,34(2):49-49.
7HU, Qi SUN, Ya-Ping WU, Yi-Kang.Conversion of N-Acyl-4-phenyl/benzyl-oxazolidine-2-thiones into Thiol Esters in the Presence of EtSH-K2CO3[J].Chinese Journal of Chemistry,2005,23(11):1561-1563.
8李昶红,谢和平,李薇,杨颖群.一维链状锌配位聚合物[Zn(4，4＇-bipy)·(o-ABA)2·(H2O)2]n的合成、晶体结构及热稳定性[J].无机化学学报,2008,24(12):2051-2055. 被引量：5
9Shun Jun JI, Zhi Liang SHEN, Shun Yi WANG College of Chemistry and Chemical Engineering, Suzhou University, Suzhou 215006.Aldol Condensation of Acetylferrocene under Ultrasound[J].Chinese Chemical Letters,2003,14(7):663-666. 被引量：3
10Wei Sham ZHOU Zheng Wu SHEN Shanghai Institute of Organic Chemistry,Chinese Academy of Science,345 Lingling Lu,Shanghai 200032.STUDY ON THE SYNTHESIS OF BRASSINOLIDE AND RELATED COMPOUNDS 15.FORMAL SYNTHESIS OF BRASSINOLIDE VIA STEREOSELECTIVE SULFENATE-SULFOXIDE TRANSFORMATION[J].Chinese Chemical Letters,1991,2(2):111-114.

Chinese Chemical Letters

2003年第9期

浏览历史

内容加载中请稍等...

Studies on the Model Synthesis of the Brassinolide and Dolicholide Side Chains

参考文献9

相关作者

相关机构

相关主题

浏览历史