Total synthesis of Amaryllidaceae alkaloids utilizing sequential intramolecular heterocyclic azadiene Diels-Alder reactions of an unsymmetrical 1,2,4,5-tetrazine

被引:73
作者
Boger, DL
Wolkenberg, SE
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
关键词
D O I
10.1021/jo0012546
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Convergent total syntheses of anhydrolycorinone, hippadine, and anhydrolycorinium chloride are detailed, enlisting sequential inverse electron demand Diels-Alder reactions of an unsymmetrical N-acyl-6-amino-1,2,4,5-tetrazine.
引用
收藏
页码:9120 / 9124
页数:5
相关论文
共 40 条
[31]   CONCISE SYNTHESIS OF NARCISSUS PYRROLOPHENANTHRIDINE ALKALOIDS - VASCONINE, ASSOANINE AND OXOASSOANINE [J].
PARNES, JS ;
CARTER, DS ;
KURZ, LJ ;
FLIPPIN, LA .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3497-3499
[32]   A NEW APPROACH TO THE SYNTHESIS OF ANTITUMOR ALKALOIDS WITH THE LYCORANE SKELETON [J].
PEREZ, D ;
GUITIAN, E ;
CASTEDO, L .
TETRAHEDRON LETTERS, 1992, 33 (17) :2407-2408
[33]   Synthesis of antitumor lycorines by intramolecular Diels-Alder reaction [J].
Perez, D ;
Bures, G ;
Guitian, E ;
Castedo, L .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) :1650-1654
[34]   ANTINEOPLASTIC AGENTS .99. AMARYLLIS-BELLADONNA [J].
PETTIT, GR ;
GADDAMIDI, V ;
GOSWAMI, A ;
CRAGG, GM .
JOURNAL OF NATURAL PRODUCTS, 1984, 47 (05) :796-801
[35]  
PRABHAKAR S, 1987, J CHEM RES, P167
[36]   CONDENSED HETEROAROMATIC RING-SYSTEMS .23. A CONCISE SYNTHESIS OF HIPPADINE [J].
SAKAMOTO, T ;
YASUHARA, A ;
KONDO, Y ;
YAMANAKA, H .
HETEROCYCLES, 1993, 36 (11) :2597-2600
[37]  
Shao HW, 1996, CHINESE CHEM LETT, V7, P13
[38]   CONCISE SYNTHESES OF THE AMARYLLIDACEAE ALKALOIDS UNGERIMINE AND HIPPADINE VIA THE SUZUKI ARYL-ARYL CROSS COUPLING REACTION [J].
SIDDIQUI, MA ;
SNIECKUS, V .
TETRAHEDRON LETTERS, 1990, 31 (11) :1523-1526
[39]   A new approach to pyrrolophenanthridone alkaloids via intramolecular radical cyclization [J].
Tsuge, O ;
Hatta, T ;
Tsuchiyama, H .
CHEMISTRY LETTERS, 1998, (02) :155-156
[40]   ANTI-LEUKEMIC ACTIVITY OF UNGEREMINE AND RELATED COMPOUNDS - PREPARATION OF ANALOGS OF UNGEREMINE BY A PRACTICAL PHOTO-CHEMICAL REACTION [J].
ZEECHENG, RKY ;
YAN, SJ ;
CHENG, CC .
JOURNAL OF MEDICINAL CHEMISTRY, 1978, 21 (02) :199-203