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 50 条

[1] ISOLATION OF ALKALOID JASMININE FROM OLEA-PANICULATA (OLEACEAE)
HART, NK
JOHNS, SR
LAMBERTON, JA
AUSTRALIAN JOURNAL OF CHEMISTRY, 1971, 24 (08) : 1739 - +
[2] FIRST TOTAL SYNTHESIS OF THE 2,7-NAPHTHYRIDINE ALKALOID NEOZEYLANICINE AND UNEXPECTED FORMATION OF ISOQUINOLINES FROM ETHOXYVINYL PYRIDINES
BRACHER, F
MINK, K
LIEBIGS ANNALEN, 1995, (04): : 645 - 647
[3] Total Synthesis of a Pyrroloindoloquinazoline Alkaloid
Gahtory, Digvijay
Chouhan, Mangilal
Sharma, Ratnesh
Nair, Vipin A.
ORGANIC LETTERS, 2013, 15 (15) : 3942 - 3945
[4] Complex alkaloid total synthesis
Movassaghi, Mohammad
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
[5] Total Synthesis of the Zoanthamine Alkaloid
M.Miyashita
复旦学报(自然科学版), 2005, (05) : 171 - 172
[6] Complex alkaloid total synthesis
Movassaghi, Mohammad
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
[7] TOTAL SYNTHESIS OF ALKALOID RHOEADINE
IRIE, H
TANI, S
YAMANE, H
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (24): : 1713 - &
[8] A TOTAL SYNTHESIS OF THE ALKALOID DEPLANCHEINE
ASHCROFT, WR
JOULE, JA
TETRAHEDRON LETTERS, 1980, 21 (24) : 2341 - 2344
[9] TOTAL SYNTHESIS OF ALKALOID, (+/-)-HASUBANONINE
IBUKA, T
TANAKA, K
INUBUSHI, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 1974, 22 (04) : 782 - 798
[10] TOTAL SYNTHESIS OF ALKALOID (+/-)-METAPHANINE
IBUKA, T
TANAKA, K
INUBUSHI, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 1974, 22 (04) : 907 - 921

← 1 2 3 4 5 →