Efficient synthesis of novel cytotoxic cis-fused α-methylene γ-lactones from 7,14-dihydroxy-ent-kaurenes by transformation under Mitsunobu reaction conditions

被引：15

作者：

Aoyagi, Y

Gui, MY

Jin, YR

Li, XW

Noguchi, T

Fukaya, H

Hasuda, T

Takeya, K

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Tokyo 1920392, Japan

[2] Jilin Univ, Dept Chem, Changchun 130021, Jilin, Peoples R China

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 07期

关键词：

natural product; semisynthesis; ent-kaurene; cytotoxic; Mitsunobu reaction conditions;

D O I：

10.1016/j.tetlet.2003.12.041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Facile transformation of 7,14-dihydroxy-ent-kaurenes such as excisanin A (8), kamebanin (9), and kamebakaurin (10), which are abundant in plants of the genus Rabdosia species (Labiatae), to ent-abietanes was accomplished under the Mitsunobu reaction conditions. The delta, epsilon-unsaturated cis-fused alpha-methylene gamma-lactones (17, 18, and 25) thus prepared showed a moderate cytotoxic activity on P388 murine leukemia cells. (C) 2003 Elsevier Ltd. All rights reserved.

引用

收藏

页码：1421 / 1425

页数：5

相关论文

共 17 条

[1] SYNTHESIS OF MONOPROTECTED 2-ALKYLIDENE-1,3-PROPANEDIOLS BY AN UNUSUAL SN2' MITSUNOBU REACTION [J].

CHARETTE, AB ;

COTE, B .

TETRAHEDRON LETTERS, 1993, 34 (43) :6833-6836

[2] Identification of new diterpenoids from Euphorbia calyptrata cell cultures [J].

CrespiPerellino, N ;

Garofano, L ;

Arlandini, E ;

Pinciroli, V ;

Minghetti, A ;

Vincieri, FF ;

Danieli, B .

JOURNAL OF NATURAL PRODUCTS, 1996, 59 (08) :773-776

[3]

GUI MY, UNPUB NAT PROD

[4] Stereostructure and bioactivities of jolkinolide D [J].

Kigoshi, H ;

Ichino, T ;

Yamada, K ;

Ijuin, Y ;

Makita, SF ;

Uemura, D .

CHEMISTRY LETTERS, 2001, (06) :518-519

[5] STRUCTURE OF KAMEBANIN, A NEW ANTI-TUMOR ENT-KAURENOID FROM ISODON-KAMEBA OKUYAMA [J].

KUBO, I ;

MIURA, I ;

KAMIKAWA, T ;

ISOBE, T ;

KUBOTA, T .

CHEMISTRY LETTERS, 1977, (11) :1289-1292

[6] Taibaihenryiin C, a diterpenoid with a novel skeleton from Isodon henryi [J].

Li, BL ;

Pan, YJ ;

Yu, KB .

TETRAHEDRON LETTERS, 2002, 43 (21) :3845-3847

[7]

LI BL, 2002, GAODENG XUEXIAO HUAX, V23, P2264

[8] Novel ent-abietane diterpenoids from Isodon eriocalyx var. laxiflora [J].

Niu, XM ;

Li, SH ;

Zhao, QS ;

Mei, SX ;

Lin, ZW ;

Sun, HD ;

Lu, Y ;

Wang, C ;

Zheng, QT .

HELVETICA CHIMICA ACTA, 2003, 86 (02) :299-306

[9] STRUCTURE OF HELIOSCOPINOLIDE-A, C20H28O3, A NOVEL DITERPENE [J].

OHBA, S ;

ITO, M ;

SAITO, Y ;

SHIZURI, Y ;

KOSEMURA, S ;

YAMAMURA, S .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1983, 39 (AUG) :1139-1141

[10] Novel rearrangement of an isocaryolane sesquiterpenoid under Mitsunobu conditions [J].

Racero, JC ;

Macías-Sánchez, AJ ;

Hernández-Galán, R ;

Hitchcock, PB ;

Hanson, JR ;

Collado, IG .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :7786-7791