An operationally simple and fully regiocontrolled formal total synthesis of the montanine-type Amaryllidaceae alkaloid (±)-pancracine

被引：21

作者：

Banwell, MG ^{[1
]}

Edwards, AJ ^{[1
]}

Jolliffe, KA ^{[1
]}

Kemmler, M ^{[1
]}

机构：

[1] Australian Natl Univ, Res Sch Chem, Inst Adv Studies, Canberra, ACT 0200, Australia

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 12期

关键词：

D O I：

10.1039/b102252k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of beta- nitrostyrene 4 with cyclohexane-1,3-dione (5) in the presence of DBU affords the Michael-addition product 6, which is readily elaborated, using straightforward chemistry, to the 5,11-methanomorphanthridine 2, acquisition of which constitutes a formal total synthesis of the racemic modification of the montanine alkaloid pancracine (1).

引用

页码：1345 / 1348

页数：4

共 33 条

[1] COMPLETION AND REFINEMENT OF CRYSTAL-STRUCTURES WITH SIR92 [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, C ;

GUAGLIARDI, A .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1993, 26 (pt 3) :343-350

[2]

[Anonymous], 1996, CAMERON

[3] FORMATION AND CRYSTAL STRUCTURE OF 3-(4-BROMOPHENYL)-2-HYDROXYIMINO-6,7-DIHYDRO-4(5H)-BENZOFURANONE - MICHAEL ADDITION OF CYCLOHEXANE-1,3-DIONE TO 4-BROMO-OMEGA-NITROSTYRENE [J].

ANSELL, GB ;

MOORE, DW ;

NIELSEN, AT .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (23) :1602-&

[4]

Brandsma L., 1998, SPRINGER LAB, P15

[5] Asymmetric catalysis .103. Enantioselective Michael addition of 1,3-dicarbonyl compounds to conjugated nitroalkenes [J].

Brunner, H ;

Kimel, B .

MONATSHEFTE FUR CHEMIE, 1996, 127 (10) :1063-1072

[6] MECHANISM OF THE MITSUNOBU ESTERIFICATION REACTION .1. THE INVOLVEMENT OF PHOSPHORANES AND OXYPHOSPHONIUM SALTS [J].

CAMP, D ;

JENKINS, ID .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3045-3049

[7] THE ALKALOIDS OF THE AMARYLLIDACEAE .4. THE ALKALOIDS OF BRUNSVIGIA COOPERI BAKER [J].

DRY, LJ ;

POYNTON, M ;

THOMPSON, ME ;

WARREN, FL .

JOURNAL OF THE CHEMICAL SOCIETY, 1958, (DEC) :4701-4704

[8] Preparation of new 2,4-disubstituted oxazoles from N-acylaziridines [J].

Eastwood, FW ;

Perlmutter, P ;

Yang, Q .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (01) :35-42

[9] LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS [J].

GEMAL, AL ;

LUCHE, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5454-5459

[10] TOTAL SYNTHESIS OF (+-)-FAWCETTIMINE [J].

HEATHCOCK, CH ;

BLUMENKOPF, TA ;

SMITH, KM .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1548-1562

← 1 2 3 4 →