First stereoselective total synthesis of macrocarpal C: structure elucidation of macrocarpal G

被引：7

作者：

Tanaka, T

Mikamiyama, H

Maeda, K

Ishida, T

In, Y

Iwata, C

机构：

[1] Osaka Univ, Fac Pharmaceut Sci, Osaka 565, Japan

[2] Osaka Univ Pharmaceut Sci, Osaka 56911, Japan

来源：

CHEMICAL COMMUNICATIONS | 1997年 / 24期

关键词：

D O I：

10.1039/a705231f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first stereoselective total synthesis of macrocarpal C is achieved via a coupling reaction of a silyl dienol ether with a novel hexasubstituted benzene chromium tricarbonyl complex as an optically active benzyl cation equivalent, thereby clarifying the identity of macrocarpal C and G.

引用

收藏

页码：2401 / 2402

页数：2

相关论文

共 21 条

[1] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[2] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[3]

DAVIES SG, 1993, SYNLETT, P323

[4]

DUGGAN ME, 1989, SYNTHESIS-STUTTGART, P131

[5] Bioactive acylphloroglucinol derivatives from Eucalyptus species [J].

Ghisalberti, EL .

PHYTOCHEMISTRY, 1996, 41 (01) :7-22

[6] ORGANOSELENIUM CHEMISTRY - FACILE ONE-STEP SYNTHESIS OF ALKYL ARYL SELENIDES FROM ALCOHOLS [J].

GRIECO, PA ;

GILMAN, S ;

NISHIZAWA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) :1485-1486

[7]

HANSSON C, 1976, SYNTHESIS-STUTTGART, P191

[8] MACROCARPAL-A, A NOVEL ANTIBACTERIAL COMPOUND FROM EUCALYPTUS-MACROCARPA [J].

MURATA, M ;

YAMAKOSHI, Y ;

HOMMA, S ;

AIDA, K ;

HORI, K ;

OHASHI, Y .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1990, 54 (12) :3221-3226

[9] MACROCARPALS, ANTIBACTERIAL COMPOUNDS FROM EUCALYPTUS, INHIBIT ALDOSE REDUCTASE [J].

MURATA, M ;

YAMAKOSHI, Y ;

HOMMA, S ;

ARAI, K ;

NAKAMURA, Y .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1992, 56 (12) :2062-2063

[10] MACROCARPALS - HIV-RTASE INHIBITORS OF EUCALYPTUS-GLOBULUS [J].

NISHIZAWA, M ;

EMURA, M ;

KAN, Y ;

YAMADA, H ;

OGAWA, K ;

HAMANAKA, N .

TETRAHEDRON LETTERS, 1992, 33 (21) :2983-2986