Total Synthesis of (-)-Conophylline and (-)-Conophyllidine

被引：43

作者：

Han-ya, Yuki ^{[1
]}

Tokuyama, Hidetoshi ^{[1
,2
]}

Fukuyama, Tohru ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

[2] Tohoku Univ, Grad Sch Pharmaceut Sci, Sendai, Miyagi 9858578, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 21期

关键词：

alkaloids; cascade reactions; heterocycles; natural products; total synthesis; TABERNAEMONTANA-DIVARICATA; NATURAL-PRODUCTS; INDOLE SYNTHESIS; CONOPHYLLINE; ALKALOIDS; PALLADIUM; LEAVES;

D O I：

10.1002/anie.201100981

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Double take: The total syntheses of the title compounds were accomplished in a highly convergent manner. The approach features the regio- and diastereoselective Polonovski-Potier-type reaction for the coupling of two aspidosperma skeletons and the formation of the dihydrofuran ring. Troc=2,2,2-trichloroethoxycarbonyl. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4884 / 4887

页数：4

共 23 条

[1] FACILE N-O BOND CLEAVAGES OF AMINE OXIDES [J].

AHOND, A ;

CAVE, A ;

KANFAN, C ;

HUSSON, HP ;

DEROSTOL.J ;

POTIER, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) :5622-&

[2]

Amino N, 1996, ANTICANCER RES, V16, P55

[3] Synthesis of the Indole Core Structures of Conophylline [J].

Ando, Shin ;

Okamoto, Yoshinari ;

Umezawa, Kazuo ;

Otsuka, Masami .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (06) :1803-1808

[4] Synthesis of vinca alkaloids and related compounds.: 100.: Stereoselective oxidation reactions of compounds with the aspidospermane and quebrachamine ring system.: First synthesis of some alkaloids containing the epoxy ring [J].

Éles, J ;

Kalaus, G ;

Greiner, I ;

Kajtár-Peredy, M ;

Szabó, P ;

Keserû, GM ;

Szabó, L ;

Szántay, C .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7255-7260

[5] Antidiabetic effect of orally administered conophylline-containing plant extract on streptozotocin-treated and Goto-Kakizaki rats [J].

Fujii, Mikio ;

Takei, Izumi ;

Umezawa, Kazuo .

BIOMEDICINE & PHARMACOTHERAPY, 2009, 63 (10) :710-716

[6] 2,4-dinitrobenzenesulfonamides: A simple and practical method for the preparation of a variety of secondary amines and diamines. [J].

Fukuyama, T ;

Cheung, M ;

Jow, CK ;

Hidai, Y ;

Kan, T .

TETRAHEDRON LETTERS, 1997, 38 (33) :5831-5834

[7] A NOVEL TIN-MEDIATED INDOLE SYNTHESIS [J].

FUKUYAMA, T ;

CHEN, XQ ;

PENG, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3127-3128

[8] NEW DIMERIC INDOLE ALKALOIDS FROM STENOSOLEN-HETEROPHYLLUS - STRUCTURE DETERMINATIONS AND SYNTHETIC APPROACH [J].

HENRIQUES, A ;

KAN, C ;

CHIARONI, A ;

RICHE, C ;

HUSSON, HP ;

KAN, SK ;

LOUNASMAA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (05) :803-811

[9] Biologically active indole and bisindole alkaloids from Tabernaemontana divaricata [J].

Kam, TS ;

Pang, HS ;

Lim, TM .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (08) :1292-1297

[10] NEW ALKALOIDS FROM THE LEAVES OF TABERNAEMONTANA-DIVARICATA [J].

KAM, TS ;

LOH, KY ;

LIM, LH ;

LOONG, WL ;

CHUAH, CH ;

WEI, C .

TETRAHEDRON LETTERS, 1992, 33 (07) :969-972

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