Practical total syntheses of epiquinamide enantiomers

被引：43

作者：

Suyama, Takashi L. ^{[1
]}

Gerwick, William H. ^{[1
]}

机构：

[1] Univ Calif San Diego, Scripps Inst Oceanog, La Jolla, CA 92093 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 20期

关键词：

D O I：

10.1021/ol061736p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Short and practical syntheses of epiquinamide and its enantiomer were accomplished with high overall yields and high stereoselectivity from readily available starting materials.

引用

页码：4541 / 4543

页数：3

共 30 条

[1] Total synthesis of the tricyclic marine alkaloids (-)-lepadiformine, (+)-cylindricine C, and (-)-fasicularin via a common intermediate formed by formic acid-induced intramolecular conjugate azaspirocyclization [J].

Abe, H ;

Aoyagi, S ;

Kibayashi, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (05) :1473-1480

[2] Recent advances in the treatment of tobacco dependence [J].

Anthenelli, RA .

CLINICAL NEUROSCIENCE RESEARCH, 2005, 5 (2-4) :175-183

[3] Small-molecule natural products: new structures, new activities [J].

Baker, DD ;

Alvi, KA .

CURRENT OPINION IN BIOTECHNOLOGY, 2004, 15 (06) :576-583

[4] An efficient method for removal of ruthenium byproducts from olefin metathesis reactions [J].

Cho, JH ;

Kim, BM .

ORGANIC LETTERS, 2003, 5 (04) :531-533

[5] Nicotinic agonists, antagonists, and modulators from natural sources [J].

Daly, JW .

CELLULAR AND MOLECULAR NEUROBIOLOGY, 2005, 25 (3-4) :513-552

[6] Bioassay-guided isolation of epiquinamide, a novel quinolizidine alkaloid and nicotinic agonist from an Ecuadoran poison frog, Epipedobates tricolor [J].

Fitch, RW ;

Garraffo, HM ;

Spande, TF ;

Yeh, HJC ;

Daly, JW .

JOURNAL OF NATURAL PRODUCTS, 2003, 66 (10) :1345-1350

[7] STEREOSPECIFIC SYNTHESIS OF (2R,3S)-3-AMINO-2-PIPERIDINEACETIC ACID-DERIVATIVES FOR USE AS CONFORMATIONAL CONSTRAINT IN PEPTIDES [J].

GOMEZMONTERREY, I ;

GONZALEZMUNIZ, R ;

HERRANZ, R ;

GARCIALOPEZ, MT .

TETRAHEDRON LETTERS, 1993, 34 (22) :3593-3594

[8] Brain neuronal nicotinic receptors as new targets for drug discovery [J].

Gotti, C ;

Riganti, L ;

Vailanti, S ;

Clementi, F .

CURRENT PHARMACEUTICAL DESIGN, 2006, 12 (04) :407-428

[9] A convenient method to remove ruthenium byproducts from olefin metathesis reactions using polymer-bound triphenylphosphine oxide (TPPO) [J].

Haack, KyoungLang ;

Ahn, Yu Mi ;

Georg, Gunda I. .

MOLECULAR DIVERSITY, 2005, 9 (04) :301-303

[10] Synthesis of a Gln-Phe hydroxy-ethylene dipeptide isostere [J].

Haug, BE ;

Rich, DH .

ORGANIC LETTERS, 2004, 6 (25) :4783-4786

← 1 2 3 →