Progress towards the total synthesis of trichodermamides A and B:: Construction of the oxazine ring moiety

被引：25

作者：

Wan, Xiaobo ^{[1
]}

Doridot, Gabriel ^{[1
]}

Joullie, Madeleine M. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 06期

关键词：

D O I：

10.1021/ol062993x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trichodermamides are modified heterocyclic dipeptides that possess a unique 4H-5,6-dihydro-1,2-oxazine ring. Starting from affordable, easily available (-)-quinic acid, the enantioselective synthesis of this oxazine moiety was achieved by an intramolecular epoxide ring-opening reaction by an oxime.

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页码：977 / 980

页数：4

相关论文

共 21 条

[1]

Al-Qawasmeh RA, 1999, CHEM LETT, P541

[2] Approaches to the synthesis of some tyrosine-derived marine sponge metabolites: Synthesis of verongamine and purealidin N [J].

Boehlow, TR ;

Harburn, JJ ;

Spilling, CD .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (09) :3111-3118

[3] Aspergillazines A-E:: novel heterocyclic dipeptides from an Australian strain of Aspergillus unilateralis [J].

Capon, RJ ;

Ratnayake, R ;

Stewart, M ;

Lacey, E ;

Tennant, S ;

Gill, JH .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) :123-129

[4] SYNTHESIS OF L-CHIRO-INOSITOL AND (-)-CONDURITOL-F FROM D-SORBITOL BY A HIGHLY STEREOSELECTIVE INTRAMOLECULAR PINACOL COUPLING PROMOTED BY SAMARIUM DIIODIDE [J].

CHIARA, JL ;

VALLE, N .

TETRAHEDRON-ASYMMETRY, 1995, 6 (08) :1895-1898

[5] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS [J].

EVANS, DA ;

BRITTON, TC ;

ELLMAN, JA ;

DOROW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4011-4030

[6] Trichodermamides A and B, cytotoxic modified Dipeptides from the marine-derived fungus Trichoderma virens [J].

Garo, E ;

Starks, CM ;

Jensen, PR ;

Fenical, W ;

Lobkovsky, E ;

Clardy, J .

JOURNAL OF NATURAL PRODUCTS, 2003, 66 (03) :423-426

[7] ADDITION AND CYCLOADDITION REACTIONS OF THE ELECTROPHILIC VINYL NITROSO-COMPOUNDS 3-NITROSOBUT-3-EN-2-ONE, 2-NITROSOPROPENAL, AND ETHYL 2-NITROSOPROPENOATE [J].

GILCHRIST, TL ;

ROBERTS, TG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (06) :1283-1292

[8] REACTION OF PYRROLES WITH ETHYL 2-NITROSO-PROPENOATES AND 2-AZO-PROPENOATES, AND WITH ETHYL CYANOFORMATE N-OXIDE - A COMPARISON OF THE REACTION PATHWAYS [J].

GILCHRIST, TL ;

LEMOS, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (13) :1391-1395

[9] REACTION OF AZOLES WITH ETHYL BROMOPYRUVATE OXIME - ALKYLATION BY SUBSTITUTION AND BY ELIMINATION ADDITION [J].

GILCHRIST, TL ;

STRETCH, W ;

CHRYSTAL, EJT .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (10) :2235-2239

[10] ETHYL 3-BROMO-2-HYDROXYIMINOPROPANOATE, A REAGENT FOR THE PREPARATION OF ETHYL-ESTERS OF ALPHA-AMINO-ACIDS [J].

GILCHRIST, TL ;

LINGHAM, DA ;

ROBERTS, TG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (23) :1089-1090