Total synthesis of (-)- and (+)-lentiginosine

被引：61

作者：

Chandra, KL ^{[1
]}

Chandrasekhar, M ^{[1
]}

Singh, VK ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 13期

关键词：

D O I：

10.1021/jo025677e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of (-)-lentiginosine was achieved from D-mannitol using highly stereoselective reactions. Similarly, (+)-lentiginosine was synthesized from L-tartaric acid.

引用

页码：4630 / 4633

页数：4

共 18 条

[1] ASSIGNMENT OF THE ABSOLUTE-CONFIGURATION OF NATURAL LENTIGINOSINE BY SYNTHESIS AND ENZYMATIC ASSAYS OF OPTICALLY PURE (+)-ENANTIOMERS AND (-)-ENANTIOMERS [J].

BRANDI, A ;

CICCHI, S ;

CORDERO, FM ;

FRIGNOLI, R ;

GOTI, A ;

PICASSO, S ;

VOGEL, P .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6806-6812

[2] SYNTHETIC APPROACHES TO STEREOISOMERS AND ANALOGS OF CASTANOSPERMINE [J].

BURGESS, K ;

HENDERSON, I .

TETRAHEDRON, 1992, 48 (20) :4045-4066

[3] An efficient strategy for the synthesis of 5-hydroxyalkylbutan-4-olides from D-mannitol: total synthesis of (-)-muricatacin [J].

Chandrasekhar, M ;

Chandra, KL ;

Singh, VK .

TETRAHEDRON LETTERS, 2002, 43 (15) :2773-2775

[4] Formal total synthesis of (+)-boronolide [J].

Chandrasekhar, M ;

Raina, S ;

Singh, VK .

TETRAHEDRON LETTERS, 2000, 41 (25) :4969-4971

[5] SYNTHESIS OF LENTIGINOSINE BY STEREOSELECTIVE CHIRAL NITRONE CYCLOADDITION AND THERMAL REARRANGEMENT OF STRAINED SPIROISOXAZOLIDINE [J].

CORDERO, FM ;

CICCHI, S ;

GOTI, A ;

BRANDI, A .

TETRAHEDRON LETTERS, 1994, 35 (06) :949-952

[6] NEW AND HIGHLY EFFECTIVE METHOD FOR OXIDATION OF PRIMARY AND SECONDARY ALCOHOLS TO CARBONYL-COMPOUNDS [J].

COREY, EJ ;

KIM, CU .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (21) :7586-&

[7] STEREOSELECTIVE TOTAL SYNTHESIS OF (+)-LENTIGINOSINE USING A CHIRAL NITRONE INTERMEDIATE [J].

GIOVANNINI, R ;

MARCANTONI, E ;

PETRINI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) :5706-5707

[8] Recent advances in olefin metathesis and its application in organic synthesis [J].

Grubbs, RH ;

Chang, S .

TETRAHEDRON, 1998, 54 (18) :4413-4450

[9] STEREOSELECTIVE SYNTHESIS OF (+)-LENIGINOSINE AND (-)-LENTIGINOSINE [J].

GURJAR, MK ;

GHOSH, L ;

SYAMALA, M ;

JAYASREE, V .

TETRAHEDRON LETTERS, 1994, 35 (47) :8871-8872

[10] ACYCLIC STEREOSELECTION .20. HIGH DIASTEREOFACIAL SELECTIVITY IN THE STANNIC CHLORIDE MEDIATED REACTIONS OF ALLYLSILANES WITH CHIRAL ALPHA-ALKOXY AND BETA-ALKOXY ALDEHYDES [J].

KIYOOKA, S ;

HEATHCOCK, CH .

TETRAHEDRON LETTERS, 1983, 24 (44) :4765-4768

← 1 2 →