Studies relating to the structure of bruceoside C: Total synthesis of the alleged aglycon of bruceoside C

被引：22

作者：

VanderRoest, JM ^{[1
]}

Grieco, PA ^{[1
]}

机构：

[1] INDIANA UNIV,DEPT CHEM,ERNEST E CAMPAIGNE & MARCUS CARMACK LAB ORGAN CHE,BLOOMINGTON,IN 47405

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 16期

关键词：

D O I：

10.1021/jo9605206

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The structures assigned to bruceoside C (1) and the derived aglycon (2) have been shown to be incorrect. The structural misassignments mere made clear by an unambiguous total synthesis of racemic 2 whose structure rests on spectral data and a single-crystal X-ray analysis of intermediate 22.

引用

页码：5316 / 5325

页数：10

共 26 条

[1] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].

ALLINGER, NL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8127-8134

[2] CONVENIENT SYNTHESIS OF 1ALPHA-HYDROXY-VITAMIN-D3 [J].

BARTON, DHR ;

HESSE, RH ;

PECHET, MM ;

RIZZARDO, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (08) :2748-2749

[3] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[4]

FREEMAN D, 1975, TETRAHEDRON LETT, P261

[5] ANTITUMOR AGENTS .127. BRUCEOSIDE-C, A NEW CYTOTOXIC QUASSINOID GLUCOSIDE, AND RELATED-COMPOUNDS FROM BRUCEA-JAVA']JAVANICA [J].

FUKAMIYA, N ;

OKANO, M ;

MIYAMOTO, M ;

TAGAHARA, K ;

LEE, KH .

JOURNAL OF NATURAL PRODUCTS, 1992, 55 (04) :468-475

[6]

Gajewski J. J., 1990, ADV MOL MODELLING, P65

[7] SYNTHETIC STUDIES ON QUASSIMARIN - CONSTRUCTION OF THE PENTACYCLIC CARBON SKELETON [J].

GRIECO, PA ;

INANAGA, J ;

SHAM, HL ;

SASAKI, S ;

KIM, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (13) :1044-1046

[8] SYNTHETIC STUDIES ON QUASSINOIDS - TOTAL SYNTHESIS OF (-)-CHAPARRINONE, (-)-GLAUCARUBOLONE, AND (+)-GLAUCARUBINONE [J].

GRIECO, PA ;

COLLINS, JL ;

MOHER, ED ;

FLECK, TJ ;

GROSS, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) :6078-6093

[9] C-19 QUASSINOIDS - TOTAL SYNTHESIS OF DL-SAMADERIN-B [J].

GRIECO, PA ;

PINEIRONUNEZ, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) :7606-7615

[10] ANTI-TUMOR AGENTS .33. ISOLATION AND STRUCTURAL ELUCIDATION OF BRUCEOSIDE-A AND BRUCEOSIDE-B, NOVEL ANTI-LEUKEMIC QUASSINOID GLYCOSIDES, AND BRUCEIN-D AND BRUCEIN-E FROM BRUCEA-JAVA']JAVANICA [J].

LEE, KH ;

IMAKURA, Y ;

SUMIDA, Y ;

WU, RY ;

HALL, IH ;

HUANG, HC .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (13) :2180-2185

← 1 2 3 →