Asymmetric Construction of Rings A-D of Daphnicyclidin-Type Alkaloids

被引:62
作者
Dunn, Travis B. [1 ]
Ellis, J. Michael [1 ]
Kofink, Christiane C. [1 ]
Manning, James R. [1 ]
Overman, Larry E. [1 ]
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
关键词
DIELS-ALDER REACTION; CARBONYL-COMPOUNDS; DAPHNIPHYLLUM; ALDEHYDES; REAGENTS; KETONES; ALPHA;
D O I
10.1021/ol902373m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The aza-Cope-Mannich reaction and ring-closing metathesis are key steps in the assembly of intermediates containing rings A-D of Daphniphyllum alkaloids of the daphnicyclidin type such as daphnipaxinin and oldhamine A.
引用
收藏
页码:5658 / 5661
页数:4
相关论文
共 21 条
[1]   New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].
Ahrendt, KA ;
Borths, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244
[2]  
[Anonymous], 1987, Hetero Diels Alder methodology in Organic Synthesis
[3]   Remarkably stable (Me3Al)2•DABCO and stereoselective nickel-catalyzed AlR3 (R = Me, Et) additions to aldehydes [J].
Biswas, K ;
Prieto, O ;
Goldsmith, PJ ;
Woodward, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (15) :2232-2234
[4]   A formal asymmetric synthesis of (-)-epibatidine using a highly diastereoselective hetero Diels-Alder reaction [J].
Cabanal-Duvillard, I ;
Berrien, JF ;
Ghosez, L ;
Husson, HP ;
Royer, J .
TETRAHEDRON, 2000, 56 (23) :3763-3769
[5]   CONJUGATE ADDITION OF THE PHENYLDIMETHYLSILYL GROUP TO ALPHA-BETA-UNSATURATED CARBONYL-COMPOUNDS USING A SILYLZINCATE IN-PLACE OF THE SILYLCUPRATE [J].
CRUMP, RANC ;
FLEMING, I ;
URCH, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (06) :701-706
[6]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[7]   A four-step synthesis of the hydroazulene core of guanacastepene [J].
Dudley, GB ;
Danishefsky, SJ .
ORGANIC LETTERS, 2001, 3 (15) :2399-2402
[8]   Carbon-carbon bond formations involving organochromium(III) reagents [J].
Fürstner, A .
CHEMICAL REVIEWS, 1999, 99 (04) :991-1045
[9]   A zwitterionic alkaloid, containing a rare cyclopentadienyl anion unit, from the stem barks of Daphniphyllum macropodum MiQ. [J].
Gan, Xian-Wen ;
Bai, Hai-Yun ;
Chen, Qi-Gang ;
Ma, Lei ;
Hu, Li-Hong .
CHEMISTRY & BIODIVERSITY, 2006, 3 (11) :1255-1259
[10]   Synthetic Studies on Daphnicyclidin A: Enantiocontrolled Construction of the BCD Ring System [J].
Ikeda, Shuhei ;
Shibuya, Masatoshi ;
Kanoh, Naoki ;
Iwabuchi, Yoshiharu .
ORGANIC LETTERS, 2009, 11 (08) :1833-1836