Synthesis of chiral 3-substituted hexahydropyrroloindoline via intermolecular cyclopropanation

被引：54
作者：
Hao Song
Jun Yang
Wei Chen
Yong Qin [1 ]
机构：
[1] W China Sch Pharm, Dept Chem Med Nat Prod, Chengdu 610041, Peoples R China
[2] W China Sch Pharm, Key Lab Drug Targeting, Chengdu 610041, Peoples R China
[3] Sichuan Univ, State Key Lab Biotherapy, Chengdu 610041, Peoples R China
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 26期
关键词：
D O I：
10.1021/ol062489s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new and efficient synthetic route to chiral 3- substituted hexahydropyrroloindoline 18 possessing absolute configurations in accordance with indole alkaloids has been developed from readily available L- tryptophan. The key step relies on the one- pot cascade reaction of oxazolidinone 17 with diazoester, which proceeds through intermolecular cyclopropanation, ring opening, and cyclization.
引用
收藏
页码：6011 / 6014
页数：4
相关论文
共 29 条
  • [1] Anthoni U, 1999, ALKAL CHEM, V13, P163, DOI 10.1016/S0735-8210(99)80025-9
  • [2] CATALYTIC ASYMMETRIC-SYNTHESIS OF EITHER ENANTIOMER OF PHYSOSTIGMINE - FORMATION OF QUATERNARY CARBON CENTERS WITH HIGH ENANTIOSELECTION BY INTRAMOLECULAR HECK REACTIONS OF (Z)-2-BUTENANILIDES
    ASHIMORI, A
    MATSUURA, T
    OVERMAN, LE
    POON, DJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) : 6949 - 6951
  • [3] Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory studies of intramolecular Heck reactions of (Z)-α,β-unsaturated anilides and mechanistic investigations of asymmetric Heck reactions proceeding via neutral intermediates
    Ashimori, A
    Bachand, B
    Calter, MA
    Govek, SP
    Overman, LE
    Poon, DJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) : 6488 - 6499
  • [4] AUSTIN JF, 2005, PNAS, V101, P5482
  • [5] BHAT B, 1993, TETRAHEDRON, V49, P10655
  • [6] Total synthesis of 5-N-acetylardeemin and amauromine:: Practical routes to potential MDR reversal agents
    Depew, KM
    Marsden, SP
    Zatorska, D
    Zatorski, A
    Bornmann, WG
    Danishefsky, SJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) : 11953 - 11963
  • [7] An expedient route to the calabar bean alkaloids (-)-physovenine and (-)-physostigmine
    El-Azab, AS
    Taniguchi, T
    Ogasawara, K
    [J]. ORGANIC LETTERS, 2000, 2 (18) : 2757 - 2759
  • [8] Stereoselective synthesis of novel conformationally restricted β- and γ-amino acids
    Gnad, F
    Poleschak, M
    Reiser, O
    [J]. TETRAHEDRON LETTERS, 2004, 45 (22) : 4277 - 4280
  • [9] Hino T., 1998, ALKALOIDS, V34, P1
  • [10] Asymmetric synthesis of pyrrolidinoindolines. Application for the practical total synthesis of (-)-phenserine
    Huang, A
    Kodanko, JJ
    Overman, LE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (43) : 14043 - 14053
123