On the identity of a neo-lignan from the fruits of Virola sebifera

被引：58

作者：

Harrowven, DC ^{[1
]}

Newman, NA ^{[1
]}

Knight, CA ^{[1
]}

机构：

[1] Univ Southampton, Dept Chem, Southampton SO17 1BJ, Hants, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 37期

关键词：

natural products; annulation; transmetallation; Heck reactions; indenes; aldol reactions;

D O I：

10.1016/S0040-4039(98)01419-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

7-(3,4-Dimethoxyphenyl)-6-methylindeno[5,6-d] [1,3]dioxol-5-one 2 has been reported as a neo-lignan isolated from the fruits of Virola sebifera. However, physical and spectroscopic data obtained from two synthetic samples of 2 do not match those quoted in the isolation paper. Data obtained from an isomer, 3-(benzo[1,3]dioxol-5-yl)-5,6-dimethoxy-2-methylinden-1-one 10, are in closer agreement but rile C-13 NMR spectrum reveals many inconsistencies. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6757 / 6760

页数：4

共 25 条

[1] 2,3-DIARYLINDENES AND 2,3-DIARYLINDENONES - SYNTHESIS, MOLECULAR-STRUCTURE, PHOTOCHEMISTRY, ESTROGEN-RECEPTOR BINDING-AFFINITY, AND COMPARISONS WITH RELATED TRIARYLETHYLENES [J].

ANSTEAD, GM ;

ALTENBACH, RJ ;

WILSON, SR ;

KATZENELLENBOGEN, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (07) :1316-1326

[2] 2-ARYLINDENES AND 2-ARYLINDENONES - MOLECULAR-STRUCTURES AND CONSIDERATIONS IN THE BINDING ORIENTATION OF UNSYMMETRICAL NONSTEROIDAL LIGANDS TO THE ESTROGEN-RECEPTOR [J].

ANSTEAD, GM ;

WILSON, SR ;

KATZENELLENBOGEN, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (09) :2163-2171

[3] ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .41. THIOENOL ETHERS BY INSERTION OF ALKYNES INTO M = C BONDS OF THIOCARBENE COMPLEXES AND DISENGAGEMENT OF LIGANDS ON SILICA-GEL [J].

AUMANN, R ;

SCHRODER, J ;

HEINEN, H .

CHEMISCHE BERICHTE, 1990, 123 (06) :1369-1374

[4] REACTION OF TRIAFULVENES WITH YNAMINES [J].

EICHER, T ;

PFISTER, T ;

URBAN, M .

CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (02) :424-450

[5] AN EFFICIENT METHOD FOR THE SYNTHESIS OF 1-ARYLALKYNES [J].

ENGLER, TA ;

COMBRINK, KD ;

RAY, JE .

SYNTHETIC COMMUNICATIONS, 1989, 19 (9-10) :1735-1744

[6]

HAJELA K, 1995, INDIAN J CHEM B, V34, P361

[7] AN INSIGHT INTO THE T-BUTYLBROMIDE DIMETHYL-SULFOXIDE REAGENT - A NOVEL APPLICATION IN LIGNAN TOTAL SYNTHESIS [J].

HARROWVEN, DC ;

DENNISON, ST .

TETRAHEDRON LETTERS, 1993, 34 (20) :3323-3326

[8] A CONCISE SYNTHESIS OF TAIWANIN-E USING A MICHAEL INITIATED RING-CLOSURE PROTOCOL [J].

HARROWVEN, DC .

TETRAHEDRON LETTERS, 1991, 32 (30) :3735-3738

[9] A triple umpolung sequence for the preparation of highly substituted indanes. [J].

Harrowven, DC ;

Browne, R .

TETRAHEDRON, 1996, 52 (47) :14951-14960

[10] THE CHEMISTRY OF BRAZILIAN MYRISTICACEAE .31. LIGNOIDS AND ARYLALKANONES FROM FRUITS OF VIROLA-ELONGATA [J].

KATO, MJ ;

YOSHIDA, M ;

GOTTLIEB, OR .

PHYTOCHEMISTRY, 1990, 29 (06) :1799-1810

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