A Biomimetic Total Synthesis of (+)-Ainsliadimer A

被引:69
作者
Li, Chao [1 ]
Yu, Xueliang [1 ]
Lei, Xiaoguang [1 ,2 ]
机构
[1] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin 300072, Peoples R China
[2] NIBS, Beijing 102206, Peoples R China
关键词
DIELS-ALDER REACTIONS; SESQUITERPENE LACTONES; NATURAL-PRODUCTS; CATALYSIS; KINETICS; KETONES; DIMER;
D O I
10.1021/ol101705j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A protecting group free and biomimetic total synthesis of (+)-ainsliadimer A has been accomplished in 14 steps from a-santonin. The synthesis relies on a hydrogen bonding promoted [4 + 2]-hetero-Diels-Alder dimerization to afford the key homodimer intermediate, which demonstrates the feasibility of using nonenzymatic conditions to achieve the proposed biosynthesis.
引用
收藏
页码:4284 / 4287
页数:4
相关论文
共 31 条
[21]   Enzymatic catalysis of the Diels-Alder reaction in the biosynthesis of natural products [J].
Oikawa, H ;
Tokiwano, T .
NATURAL PRODUCT REPORTS, 2004, 21 (03) :321-352
[22]  
PIERS E, 1969, CHEM COMMUN, P562
[23]   Chemistry and biology of biosynthetic Diels-Alder reactions [J].
Stocking, EM ;
Williams, RM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (27) :3078-3115
[24]  
Tamura R, 1998, ENANTIOMER, V3, P149
[25]   Enantioselective Diels-Alder reactions catalyzed by hydrogen bonding [J].
Thadani, AN ;
Stankovic, AR ;
Rawal, VH .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (16) :5846-5850
[26]   Axially chiral biaryl diols catalyze highly enantioselective hetero-Diels-Alder reactions through hydrogen bonding [J].
Unni, AK ;
Takenaka, N ;
Yamamoto, H ;
Rawal, VH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (05) :1336-1337
[27]   Effect of Intramolecular Paterno-Buchi Reaction on the Thermodynamics and Kinetics of Nearly Degenerate [3,3]-Sigmatropic Shift in Fluxional Polycycles [J].
Valiulin, Roman A. ;
Dressen, Donald G. ;
Riggs, Jennifer R. ;
Habte, Faven M. ;
Kutateladze, Andrei G. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09) :3484-3490
[28]   Ainsliadimer A, A new sesquiterpene lactone dimer with an unusual carbon skeleton from Ainsliaea macrocephala [J].
Wu, Zhi-Jun ;
Xu, Xi-Ke ;
Shen, Yun-Heng ;
Su, Juan ;
Tian, Jun-Mian ;
Liang, Shuang ;
Li, Hui-Liang ;
Liu, Rui-Hui ;
Zhang, Wei-Dong .
ORGANIC LETTERS, 2008, 10 (12) :2397-2400
[29]   A case study in biomimetic total synthesis: Polyolefin carbocyclizations to terpenes and steroids [J].
Yoder, RA ;
Johnston, JN .
CHEMICAL REVIEWS, 2005, 105 (12) :4730-4756
[30]  
Young IS, 2009, NAT CHEM, V1, P193, DOI [10.1038/NCHEM.216, 10.1038/nchem.216]