Enantioselective total synthesis of (+)-galbulin via organocatalytic domino Michael-Michael-aldol condensation

被引:37
作者
Hong, Bor-Cherng [1 ]
Hsu, Che-Sheng [1 ]
Lee, Gene-Hsiang [2 ]
机构
[1] Natl Chung Cheng Univ, Dept Chem & Biochem, Chiayi 621, Taiwan
[2] Natl Taiwan Univ, Instrumentat Ctr, Taipei 106, Taiwan
关键词
ASYMMETRIC-SYNTHESIS; CASCADE REACTIONS; NATURAL-PRODUCTS; LIGNANS; ANALOGS; EPIPODOPHYLLOTOXIN; STEREOCHEMISTRY; PODOPHYLLOTOXIN; (+/-)-GALBULIN; CHEMISTRY;
D O I
10.1039/c2cc16682h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A concise and practical enantioselective synthesis of (+)-galbulin has been achieved using organocatalytic domino Michael-Michael-aldol condensation and organocatalytic kinetic resolution as the key steps.
引用
收藏
页码:2385 / 2387
页数:3
相关论文
共 56 条
[1]  
Ayres D. C., 1990, LIGNANS CHEM BBIOLOG
[2]   Enzyme-assisted asymmetric total synthesis of (-)-podophyllotoxin and (-)-picropodophyllin [J].
Berkowitz, DB ;
Choi, S ;
Maeng, JH .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (03) :847-860
[3]   Novel "Reverse Kahne-type glycosylation": Access to O-, N-, and C-linked epipodophyllotoxin conjugates [J].
Berkowitz, DB ;
Choi, SJ ;
Bhuniya, D ;
Shoemaker, RK .
ORGANIC LETTERS, 2000, 2 (08) :1149-1152
[4]   SYNTHESES OF LIGNANS FROM 2,3-DIAROYLBUTANES [J].
BIFTU, T ;
HAZRA, BG ;
STEVENSON, R ;
WILLIAMS, JR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (10) :1147-1150
[5]   SOME STEREOCHEMICAL STUDIES OF LIGNANS [J].
BIRCH, AJ ;
MILLIGAN, B ;
SMITH, E ;
SPEAKE, RN .
JOURNAL OF THE CHEMICAL SOCIETY, 1958, (DEC) :4471-4476
[6]   1ST TOTAL SYNTHESIS OF (-)-ALPHA-CONIDENDRIN [J].
BOISSIN, P ;
DHAL, R ;
BROWN, E .
TETRAHEDRON LETTERS, 1989, 30 (33) :4371-4374
[7]   OXIDATIVE COUPLING OF LIGNANS .2. NON-PHENOLIC COUPLING OF DIARYLBUTANE LIGNANS RELATED TO MATAIRESINOL DIMETHYL ETHER [J].
BUCKLETON, JS ;
CAMBIE, RC ;
CLARK, GR ;
CRAW, PA ;
RICKARD, CEF ;
RUTLEDGE, PS ;
WOODGATE, PD .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1988, 41 (03) :305-324
[8]   CONSTITUTION OF RESIN PHENOLS AND THEIR BIOGENETIC RELATIONS .18. CONVERSION OF ALPHA-CONIDENDRIN TO GALBULIN [J].
CARNMALM, B .
ACTA CHEMICA SCANDINAVICA, 1954, 8 (10) :1827-1829
[9]   A concise stereocontrolled formal total synthesis of (±)-podophyllotoxin using sulfoxide chemistry [J].
Casey, M ;
Keaveney, CM .
CHEMICAL COMMUNICATIONS, 2004, (02) :184-185
[10]   NATURALLY OCCURRING OXYGEN HETEROCYCLICS .11. VERAGUENSIN [J].
CROSSLEY, NS ;
DJERASSI, C .
JOURNAL OF THE CHEMICAL SOCIETY, 1962, (APR) :1459-&