Total syntheses of (-)-α-kainic acid and (+)-α-allokainic acid via stereoselective C-H insertion and efficient 3,4-stereocontrol

被引：54
|
作者：
Jung, Young Chun [1 ,2 ,3 ]
Yoon, Cheol Hwan [1 ,2 ,3 ]
Turos, Edward [1 ,2 ,3 ]
Yoo, Kyung Soo [1 ,2 ,3 ]
Jung, Kyung Woon [1 ,2 ,3 ]
机构：
[1] Univ So Calif, Loker Hydrocarbon Res Inst, Los Angeles, CA 90089 USA
[2] Univ So Calif, Dept Chem, Los Angeles, CA 90089 USA
[3] Univ S Florida, Dept Chem, Tampa, FL 33620 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 26期
关键词：
D O I：
10.1021/jo701988j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reported herein is a novel approach to the total syntheses of (-)-alpha-kainic acid and (+)-alpha-allokainic acid, where the stereochemistries on C(2), C(3), and C(4) of the pyrrolidine core were introduced efficiently and selectively. A regio- and stereoselective C-H insertion reaction was utilized to prepare the gamma-lactam as an intermediate. A Michael-type cyclization of phenylsulfone with a conjugated acetylenic ketone was developed to prepare the tricyclic ketone as a key intermediate for (-)-alpha-kainic acid. Subsequently, a stereoselective dephenylsulfonylation was carried out successfully to secure the cis relationship at C(3) and C(4) centers. An unprecedented acetylation on the phenylsulfone, followed by a stereoselective dephenylsulfonylation, secured the trans relationship at C(3) and C(4) centers in (+)-alpha-allokainic acid.
引用
收藏
页码：10114 / 10122
页数：9
相关论文
共 50 条
  • [21] Divergent Total Syntheses of Lycorine Alkaloids via a Sequential C-H Functionalization Strategy
    Chen, Yang
    Cha, Tong-Ling
    Jiang, Jing
    Li, Yong
    Xie, Xiao-Yan
    Li, Dashan
    Yan, Cai-Xian
    Shao, Li-Dong
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (07): : 4851 - 4860
  • [22] 3-Pyrrolines via alkylidene carbene C-H insertion: Toward the total synthesis of (+)-lactacystin.
    Wardrop, DJ
    Bowen, EG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U74 - U74
  • [23] CO2 insertion into C-H bonds for carboxylic acid synthesis
    Xiao, Dianne
    Chant, Emma
    Yau, Allison
    Kanan, Matthew
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [24] Arene C-H insertion catalyzed by ferrocene covalently heterogenized on graphene acid
    Mosconi, Dario
    Blanco, Matias
    Gatti, Teresa
    Calvillo, Laura
    Otyepka, Michal
    Bakandritsos, Aristides
    Menna, Enzo
    Agnoli, Stefano
    Granozzi, Gaetano
    CARBON, 2019, 143 : 318 - 328
  • [25] Rhodium catalysed reactions of silylated diazoacetates:: Stereoselective synthesis of α-silylated γ-lactones via C-H insertion
    Marsden, SP
    Pang, WK
    TETRAHEDRON LETTERS, 1998, 39 (33) : 6077 - 6080
  • [26] Stereoselective intramolecular 1,3 C-H insertion in Rh(II) carbene reactions
    Shi, WF
    Zhang, B
    Zhang, J
    Liu, BG
    Zhang, SW
    Wang, JB
    ORGANIC LETTERS, 2005, 7 (14) : 3103 - 3106
  • [27] Total synthesis of (+)-lithospermic acid by asymmetric intramolecular alkylation via catalytic C-H bond activation
    O'Malley, SJ
    Tan, KL
    Watzke, A
    Bergman, RG
    Ellman, JA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (39) : 13496 - 13497
  • [28] Enantioselective total synthesis of (-)-kainic acid and (+)-acromelic acid C via Rh(I)-catalyzed asymmetric enyne cycloisomerization
    Lei, Honghui
    Xin, Shan
    Qiu, Yifan
    Zhang, Xumu
    CHEMICAL COMMUNICATIONS, 2018, 54 (07) : 727 - 730
  • [29] Alkenyl C-H insertion of iodonium ylides into pyrroles: Studies toward the total syntheses of tolmetin and amtolmetin guacil
    Batsila, C
    Gogonas, EP
    Kostakis, G
    Hadjiarapoglou, LP
    ORGANIC LETTERS, 2003, 5 (09) : 1511 - 1514
  • [30] The silver salt of 12-tungstophosphoric acid:: A mild and selective catalyst for the synthesis of β-ketoesters via C-H insertion
    Yadav, J. S.
    Reddy, B. V. Subba
    Purnima, K. V.
    Jhansi, S.
    Nagaiah, K.
    Lingaiah, N.
    CATALYSIS COMMUNICATIONS, 2008, 9 (14) : 2361 - 2364
12345