Gymnothelignans A-O: Conformation and Absolute Configuration Analyses of Lignans Bearing Tetrahydrofuran from Gymnotheca chinensis

被引：34

作者：

He, Dahai ^{[1
]}

Ding, Lisheng ^{[1
]}

Xu, Hongxi ^{[2
]}

Lei, Xinxiang ^{[3
]}

Xiao, Hongping ^{[3
]}

Zhou, Yan ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Biol, Key Lab Mt Ecol Restorat & Bioresource Utilizat, Chengdu 610041, Peoples R China

[2] Shanghai Univ Tradit Chinese Med, Shanghai 201203, Peoples R China

[3] Wenzhou Univ, Wenzhou 325035, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 19期

关键词：

PUTATIVE STRUCTURE; CONSTITUENTS; EUPOMATILONE-6; DERIVATIVES;

D O I：

10.1021/jo301225v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fifteen new lignans, gymnothelignans A-O (1-15), bearing tetrahydrofuran with variable conformations belonging to three potentially related skeletons were isolated from Gymnotheca chinensis Decne. The structures were elucidated by means of detailed spectroscopic analysis. Absolute configurations were assigned using X-ray single-crystal diffraction and chemical transformations. Moreover, by the homology, compounds 1-11 and eupomatilones were confirmed to have uniform R-configuration at C-5. However, a synthesized congener has long been mistaken as 5-epimer of eupomatilone-6. This work provides guidance for the absolute configuration establishment of the subeupomatilone family with trans-H-4 H-5 configuration.

引用

页码：8435 / 8443

页数：9

共 31 条

[1]

BOHLMANN F, 1976, CHEM BER-RECL, V109, P3366, DOI 10.1002/cber.19761091013

[2] CONSTITUENTS OF EUPOMATIA SPECIES .7. DIENONE-PHENOL AND DIENOL-BENZENE REARRANGEMENTS IN THE EUPODIENONE-1 SERIES [J].

BOWDEN, BF ;

READ, RW ;

TAYLOR, WC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (04) :799-817

[3] CONSTITUENTS OF EUPOMATIA SPECIES .14. THE STRUCTURES OF EUPOMATILONE-1, EUPOMATILONE-2, EUPOMATILONE-3, EUPOMATILONE-4, EUPOMATILONE-5, EUPOMATILONE-6 AND EUPOMATILONE-7 ISOLATED FROM EUPOMATIA-BENNETTII [J].

CARROLL, AR ;

TAYLOR, WC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (12) :1705-1714

[4] CONSTITUENTS OF EUPOMATIA SPECIES .12. ISOLATION OF CONSTITUENTS OF THE TUBERS AND AERIAL PARTS OF EUPOMATIA-BENNETTII AND DETERMINATION OF THE STRUCTURES OF NEW ALKALOIDS FROM THE AERIAL PARTS OF E-BENNETTII AND MINOR ALKALOIDS OF E-LAURINA [J].

CARROLL, AR ;

TAYLOR, WC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (11) :1615-1626

[5] Total synthesis of eupomatilones 4 and 6: Structurally rearranged and atropisomerically fluxional lignan natural products [J].

Coleman, RS ;

Gurrala, SR .

ORGANIC LETTERS, 2004, 6 (22) :4025-4028

[6] ON ENANTIOMORPH-POLARITY ESTIMATION [J].

FLACK, HD .

ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV) :876-881

[7] 4,5-DIHYDROBLUMENOL A, A NEW NOR-ISOPRENOID FROM PERROTTETIA-MULTIFLORA [J].

GONZALEZ, AG ;

GUILLERMO, JA ;

RAVELO, AG ;

JIMENEZ, IA ;

GUPTA, MP .

JOURNAL OF NATURAL PRODUCTS, 1994, 57 (03) :400-402

[8] Synthesis of eupomatilone-6 and assignment of its absolute configuration [J].

Gurjar, MK ;

Karumudi, B ;

Ramana, CV .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) :9658-9661

[9] Synthesis of the putative structure of eupomatilone-6 [J].

Gurjar, MK ;

Cherian, J ;

Ramana, CV .

ORGANIC LETTERS, 2004, 6 (03) :317-319

[10] Oblongifolins A-D, polyprenylated benzoylphloroglucinol derivatives from Garcinia oblongifolia [J].

Hamed, Wafaa ;

Brajeul, Solenn ;

Mahuteau-Betzer, Florence ;

Thoison, Odile ;

Mons, Stephane ;

Delpech, Bernard ;

Van Hung, Nguyen ;

Sevenet, Thierry ;

Marazano, Christian .

JOURNAL OF NATURAL PRODUCTS, 2006, 69 (05) :774-777

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