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

页码：10114 / 10122

页数：9

共 50 条

[1] Total syntheses of (-)-α-kainic acid and (+)-α-allokainic acid via stereoselective C-H insertion and efficient 3,4-stereocontrol (vol 117, pg 5757, 1995)
Jung, Young Chun
Yoon, Cheol Hwan
Turos, Edward
Yoo, Kyung Soo
Jung, Kyung Woon
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (07): : 2959 - 2959
[2] Asymmetric total syntheses of (-)-a-kainic acid and (+)-a-allokainic acid
Li, Ang
Yang, Licheng
Deng, Jun
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
[3] A concise synthesis of (+)-α-allokainic acid via site- and diastereoselective intramolecular C-H insertion process
Anada, M
Sugimoto, T
Watanabe, N
Nakajima, M
Hashimoto, S
HETEROCYCLES, 1999, 50 (02) : 969 - 980
[4] Total Synthesis of (±)-Kainic Acid: A Photochemical C-H Carbamoylation Approach
Kamon, Takuma
Irifune, Yayoi
Tanaka, Tetsuaki
Yoshimitsu, Takehiko
ORGANIC LETTERS, 2011, 13 (10) : 2674 - 2677
[5] Asymmetric synthesis of β-hydroxy acid via stereoselective dirhodium(II)-catalyzed C-H insertion of α-alkoxydiazoketone
Yakura, T
Tanaka, T
Ikeda, M
Uenishi, J
CHEMICAL & PHARMACEUTICAL BULLETIN, 2003, 51 (04) : 471 - 473
[6] Stereoselective Synthesis of (-)-a-Kainic Acid and (+)-a-Allokainic Acid via Trimethylstannyl-Mediated Radical Carbocyclization and Oxidative Destannylation
Hanessian, S.
Ninkovic, S.
Journal of Organic Chemistry, 61 (16):
[7] Cu-exchanged phosphotungestic acid: An efficient and reusable heteropoly acid for the cyclopropanation of alkenes via C-H insertion
Yadav, J. S.
Reddy, B. V. Subba
Purnima, K. V.
Nagaiah, K.
Lingaiah, N.
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2008, 285 (1-2) : 36 - 40
[8] Stereoselective synthesis of (-)-alpha-kainic acid and (+)-alpha-allokainic acid via trimethylstannyl-mediated radical carbocyclization and oxidative destannylation
Hanessian, S
Ninkovic, S
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16): : 5418 - 5424
[9] Two syntheses of (-)-kainic acid via highly stereoselective zinc-ene cyclizations
Chalker, Justin M.
Yang, Ao
Deng, Kai
Cohen, Theodore
ORGANIC LETTERS, 2007, 9 (19) : 3825 - 3828
[10] Efficient synthesis of cholic acid derivates through stereoselective C-H functionalization from hyodeoxycholic acid
Liang, Yu-Yan
Huang, Huan
Li, Yang
Du, Rong-Kai
Li, Jing
Liu, Yong-Hong
Li, Shan
Zhang, Lei
STEROIDS, 2020, 157

← 1 2 3 4 5 →