Synthesis of C-7 oxidized abietane diterpenes from racemic ferruginyl methyl ether

被引：32

作者：

Li, AP ^{[1
]}

She, XG ^{[1
]}

Zhang, JY ^{[1
]}

Wu, TX ^{[1
]}

Pan, XF ^{[1
]}

机构：

[1] Lanzhou Univ, Dept Chem, Natl Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

TETRAHEDRON | 2003年 / 59卷 / 30期

基金：

中国国家自然科学基金;

关键词：

abietane; terpenes and terpenoids; biologically active compounds; X-ray crystal structures;

D O I：

10.1016/S0040-4020(03)00883-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of naturally occurring C-7 oxidized abietane diterpenes have been synthesized from racemic ferruginyl methyl ether in high yields. 6-Hydroxyl-5,6-dehydrosugiol (7) can be converted into stable xanthoperol (12) using high temperature. Among the products, the structures of sugiyl methyl ether (2) and 6(-hydroxysugiyl methyl ether (8) were determined by X-ray analysis. (C) 2003 Published by Elsevier Science Ltd.

引用

页码：5737 / 5741

页数：5

共 25 条

[1] ANTIMALARIAL COMPOUNDS FROM HOSLUNDIA-OPPOSITA [J].

ACHENBACH, H ;

WAIBEL, R ;

NKUNYA, MHH ;

WEENEN, H .

PHYTOCHEMISTRY, 1992, 31 (11) :3781-3784

[2] AN ANTIMICROBIAL ABIETANE FROM THE ROOT OF PLECTRANTHUS-HEREROENSIS [J].

BATISTA, O ;

SIMOES, MF ;

DUARTE, A ;

VALDEIRA, ML ;

DELATORRE, MC ;

RODRIGUEZ, B .

PHYTOCHEMISTRY, 1995, 38 (01) :167-169

[3] CONSTITUENTS OF THE WOOD OF JUNIPERUS-COMMUNIS L [J].

BREDENBERG, JBS ;

GRIPENBERG, J .

ACTA CHEMICA SCANDINAVICA, 1956, 10 (10) :1511-1514

[4] Antimicrobial abietane diterpenoids from Plectranthus elegans [J].

Dellar, JE ;

Cole, MD ;

Waterman, PG .

PHYTOCHEMISTRY, 1996, 41 (03) :735-738

[5] ON THE DIRECT FORMATION OF EPISULFONIUM IONS FROM ALKENES - AN APPLICATION TO THE SYNTHESIS OF HIGHER-ORDER CARBOCYCLES VIA EPISULFONIUM ION INITIATED POLYENE CYCLIZATIONS [J].

EDSTROM, ED ;

LIVINGHOUSE, T .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05) :949-951

[6] A NEW GENERAL SYNTHETIC APPROACH TO DITERPENES - APPLICATION TO SYNTHESES OF (+/-)-TAXODIONE AND (+/-)-ROYLEANONE [J].

ENGLER, TA ;

SAMPATH, U ;

NAGANATHAN, S ;

VELDE, DV ;

TAKUSAGAWA, F ;

YOHANNES, D .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (24) :5712-5727

[7]

ERNST W, 1965, J ORG CHEM, V30, P713

[8] Stereoselective synthesis of (-)-6,7-dehydroferruginyl methyl ether [J].

Gan, YH ;

Li, AP ;

Pan, XF ;

Chan, ASC ;

Yang, TK .

TETRAHEDRON-ASYMMETRY, 2000, 11 (03) :781-787

[9]

Gao JJ, 1997, PHYTOCHEMISTRY, V44, P759, DOI 10.1016/S0031-9422(96)00609-7

[10] Anti-tumor promoting diterpenes from the stem bark of Thuja standishii (Cupressaceae) [J].

Iwamoto, M ;

Ohtsu, H ;

Tokuda, H ;

Nishino, H ;

Matsunaga, S ;

Tanaka, R .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (07) :1911-1921

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