Total synthesis of the naphthyridine alkaloid jasminine

被引：10

作者：

Bennasar, ML ^{[1
]}

Roca, T ^{[1
]}

Zulaica, E ^{[1
]}

Monerris, M ^{[1
]}

机构：

[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain

来源：

TETRAHEDRON | 2004年 / 60卷 / 32期

关键词：

dihydropyridines; pyridines; acylation; alkaloids;

D O I：

10.1016/j.tet.2004.06.027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of (+/-)-jasminine (1), a member of a small group of naphthyridine alkaloids, has been achieved. The synthetic route takes advantage of the reactivity of dihydropyridine intermediates for the preparation of trisubstituted pyridine 4, which gives access to the alkaloid by a reductive amination-lactamization tandem reaction. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：6785 / 6789

页数：5

共 34 条

[1] ABDELMAGID AF, 1994, SYNLETT, P81
[2] REDUCTIVE AMINATION OF ALDEHYDES AND KETONES BY USING SODIUM TRIACETOXYBOROHYDRIDE
ABDELMAGID, AF
MARYANOFF, CA
CARSON, KG
[J]. TETRAHEDRON LETTERS, 1990, 31 (39) : 5595 - 5598
[3] Bae JW, 2000, J CHEM SOC PERK T 1, P145
[4] Monoterpene alkaloids, iridoids and phenylpropanoid glycosides from Osmanthus austrocaledonica
Benkrief, R
Ranarivelo, Y
Skaltsounis, AL
Tillequin, F
Koch, M
Pusset, J
Sévenet, T
[J]. PHYTOCHEMISTRY, 1998, 47 (05) : 825 - 832
[5] Total synthesis of the proposed structures of indole alkaloids lyaline and lyadine
Bennasar, ML
Roca, T
Monerris, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (03) : 752 - 756
[6] A synthetic entry to 3,5-disubstituted pyridines
Bennasar, ML
Zulaica, E
Roca, T
Alonso, Y
Monerris, M
[J]. TETRAHEDRON LETTERS, 2003, 44 (25) : 4711 - 4714
[7] Bennasar ML, 2000, EUR J ORG CHEM, V2000, P3919, DOI 10.1002/1099-0690(200012)2000:23<3919::AID-EJOC3919>3.0.CO
[8] 2-P
[9] Addition of ester enolates to N-alkyl-2-fluoropyridinium salts:: Total synthesis of (±)-20-deoxycamptothecin and (+)-camptothecin
Bennasar, ML
Zulaica, E
Juan, C
Alonso, Y
Bosch, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) : 7465 - 7474
[10] Synthesis of 4-functionalized aryl-3,5-diacyl-1,4-dihydropyridines
Bennasar, ML
Roca, T
Monerris, M
Juan, C
Bosch, J
[J]. TETRAHEDRON, 2002, 58 (40) : 8099 - 8106

← 1 2 3 4 →