A concise synthesis of d,l-brevianamide B via a biomimetically-inspired IMDA construction

被引:62
作者
Adams, Luke A.
Valente, Meriah W. N.
Williams, Robert M. [1 ]
机构
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
[2] Univ Colorado, Ctr Canc, Aurora, CO 80045 USA
基金
美国国家卫生研究院;
关键词
Fisher indole; intramolecular Diels-Alder; azadiene; brevianamide B;
D O I
10.1016/j.tet.2005.11.097
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise synthesis of brevianamide B has been accomplished using a biomimetically-inspired intramolecular Diels-Alder reaction to diastereoselectively form the characteristic bicyclo[2.2.2]diazooctane core. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5195 / 5200
页数:6
相关论文
共 36 条
[1]   Concise synthesis of the core bicyclo[2.2.2]diazaoctane ring common to asperparaline, paraherquamide, and stephacidin alkaloids [J].
Adams, LA ;
Gray, CR ;
Williams, RM .
TETRAHEDRON LETTERS, 2004, 45 (23) :4489-4493
[2]   STUDIES IN RELATION TO BIOSYNTHESIS .44. STRUCTURAL ELUCIDATIONS OF BREVIANAMIDE-B, BREVIANAMIDE-C, BREVIANAMIDE-D AND BREVIANAMIDE-F [J].
BIRCH, AJ ;
RUSSELL, RA .
TETRAHEDRON, 1972, 28 (11) :2999-&
[3]   STUDIES IN RELATION TO BIOSYNTHESIS .42. STRUCTURAL ELUCIDATION AND SOME ASPECTS OF BIOSYNTHESIS OF BREVIANAMIDES-A AND BREVIANAMIDES-E [J].
BIRCH, AJ ;
WRIGHT, JJ .
TETRAHEDRON, 1970, 26 (10) :2329-&
[4]  
BIRCH AJ, 1969, J CHEM SOC CHEM COMM, P644
[5]   OXIDATIVE HYDROLYSIS OF 1,3-DITHIANE DERIVATIVES TO CARBONYL COMPOUNDS USING N-HALOSUCCINIMIDE REAGENTS [J].
COREY, EJ ;
ERICKSON, BW .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (23) :3553-&
[6]  
CUTRONE JQ, 2001, Patent No. 6291461
[7]   PHOTOCHEMISTRY OF 1,5-HEXADIEN-3-ONES - WAVELENGTH-DEPENDENT SELECTIVITY IN INTRAMOLECULAR ENONE-OLEFIN PHOTOADDITIONS [J].
DAUBEN, WG ;
COGEN, JM ;
GANZER, GA ;
BEHAR, V .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (15) :5817-5824
[8]   Studies on the biosynthesis of paraherquamide A and VM99955.: A theoretical study of intramolecular Diels-Alder cycloaddition [J].
Domingo, LR ;
Zaragozá, RJ ;
Williams, RM .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2895-2902
[9]   Biosynthesis of the brevianamides. An ab initio study of the biosynthetic intramolecular Diels-Alder cycloaddition [J].
Domingo, LR ;
SanzCervera, JF ;
Williams, RM ;
Picher, MT ;
Marco, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1662-1667
[10]   PHOTOCHEMISTRY OF SUBSTITUTED 1,5-HEXADIEN-3-ONES [J].
GIBSON, TW ;
ERMAN, WF .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (08) :1148-&