An expeditious synthesis of nocardiolactone

被引：11
|
作者：
Sun, YP [1 ]
Wu, YK [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
来源：
SYNLETT | 2005年 / 09期
关键词：
asymmetric synthesis; chiral auxiliaries; lactones; ring contractions; total synthesis;
D O I：
10.1055/s-2005-869832
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Nocardiolactone was synthesized by using a Crimmins asymmetric aldolization followed by a DMAP-mediated removal of the auxiliary with concurrent protection of the carboxylic group as a benzyl ester, activation of the beta-hydroxyl group as a mesylate, hydrogenolysis of the benzyl ester, and a novel DBU-mediated lactonization that converted the syn-configuration to the trans one.
引用
收藏
页码：1477 / 1479
页数：3
相关论文
共 50 条
  • [31] An expeditious formal synthesis of(-)-epibalidine
    Cabanal-Duvillard, I
    Berrien, JF
    Royer, J
    TETRAHEDRON-ASYMMETRY, 2000, 11 (12) : 2525 - 2529
  • [32] An expeditious route to the synthesis of kelampayosides A and B
    Duynstee, HI
    de Koning, MC
    van der Marel, GA
    van Boom, JH
    TETRAHEDRON, 1999, 55 (32) : 9881 - 9898
  • [33] An Expeditious Synthesis of 1-Thiotrehalose
    Tardieu, Damien
    Davila, Maria F. Cespedes
    Hazelard, Damien
    Compain, Philippe
    SYNTHESIS-STUTTGART, 2018, 50 (19): : 3927 - 3930
  • [34] An expeditious synthesis of a biscyclam with an aromatic linker
    Xu, DQ
    Mattner, PG
    Prasad, K
    Repic, O
    Blacklock, TJ
    TETRAHEDRON LETTERS, 1996, 37 (30) : 5301 - 5304
  • [35] A novel, expeditious synthesis of racemic camptothecin
    Anderson, RJ
    Raolji, GB
    Kanazawa, A
    Greene, AE
    ORGANIC LETTERS, 2005, 7 (14) : 2989 - 2991
  • [36] AN EXPEDITIOUS AND EFFICIENT FORMAL SYNTHESIS OF (+/-)-APHIDICOLIN
    TOYOTA, M
    NISHIKAWA, Y
    FUKUMOTO, K
    TETRAHEDRON LETTERS, 1994, 35 (35) : 6495 - 6498
  • [37] Expeditious Access to Morphinans by Chemical Synthesis
    White, Lorenzo V.
    Hu, Nan
    He, Yu-Tao
    Banwell, Martin G.
    Lan, Ping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (27)
  • [38] An expeditious enantioselective total synthesis of valilactone
    Wu, Yikang
    Sun, Ya-Ping
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (15): : 5748 - 5751
  • [39] AN EXPEDITIOUS SYNTHESIS OF DITHIOACETALS USING ZEOLITES
    KUMAR, P
    REDDY, RS
    SINGH, AP
    PANDEY, B
    SYNTHESIS-STUTTGART, 1993, (01): : 67 - 69
  • [40] AN EXPEDITIOUS SYNTHESIS OF DOLASTATIN-10
    TOMIOKA, K
    KANAI, M
    KOGA, K
    TETRAHEDRON LETTERS, 1991, 32 (21) : 2395 - 2398
12345