First asymmetric total synthesis of Us-7 and-8, novel D-seco corynanthe-type oxindole alkaloids from Uncaria attenuata:: Structure revision of Us-7 and determination of absolute stereochemistry

被引：40

作者：

Takayama, H ^{[1
]}

Fujiwara, R ^{[1
]}

Kasai, Y ^{[1
]}

Kitajima, M ^{[1
]}

Aimi, N ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 16期

关键词：

D O I：

10.1021/ol035128a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting from (S)-glycidol, the asymmetric total synthesis of novel D-seco Corynanthe-type oxindoles Us-7 and Us-8 was accomplished. The structure of Us-7 was revised from the reported structure 1 with the (3R,7S) form to structure 22 with (3S,7R), and the absolute stereochemistry at C15 of both alkaloids was established.

引用

页码：2967 / 2970

页数：4

共 45 条

[1] Structures of Us-7 and Us-8: A new type of oxindole alkaloids isolated from Uncaria attenuata Korth [J].

Aimi, N ;

Shimizu, T ;

Sada, H ;

Takayama, H ;

Sakai, S ;

Wongseripipatana, S ;

Ponglux, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (03) :187-188

[2] THE CHLOROINDOLENINE IMINO ETHER OXINDOLE SEQUENCE - A REEXAMINATION [J].

AWANG, DVC ;

VINCENT, A ;

KINDACK, D .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (12) :2667-2675

[3]

BASHA A, 1977, TETRAHEDRON LETT, P4171

[4] Enantioselective hydrogenation of β-keto sulfones with chiral Ru(II)-catalysts:: synthesis of enantiomerically pure butenolides and γ-butyrolactones [J].

Bertus, P ;

Phansavath, P ;

Ratovelomanana-Vidal, V ;

Genêt, JP ;

Touati, AR ;

Homri, T ;

Hassine, BB .

TETRAHEDRON-ASYMMETRY, 1999, 10 (07) :1369-1380

[5] SYNTHESIS OF (-)-(6R,10R)-MATSUONE - ASSIGNMENT OF RELATIVE STEREOCHEMISTRY TO A PHEROMONE OF MATSUCOCCUS PINE BAST SCALES [J].

CYWIN, CL ;

WEBSTER, FX ;

KALLMERTEN, J .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :2953-2955

[6] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[7] Total synthesis of spirotryprostatin A, leading to the discovery of some biologically promising analogues [J].

Edmondson, S ;

Danishefsky, SJ ;

Sepp-Lorenzino, L ;

Rosen, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (10) :2147-2155

[8]

ESMOND R, 1980, J AM CHEM SOC, V102, P7117

[9] OXIDATIVE TRANSFORMATIONS OF INDOLE ALKALOIDS .1. PREPARATION OF OXINDOLES FROM YOHIMBINE - STRUCTURES AND PARTIAL SYNTHESES OF MITRAPHYLLINE, RHYNCOPHYLLINE AND CORYNOXEINE [J].

FINCH, N ;

TAYLOR, WI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (20) :3871-+

[10] OXIDATIVE TRANSFORMATIONS OF INDOLE ALKALOIDS .2. PREPARATION OF OXINDOLES FROM CIS-DE-YOHIMBINOID - PARTIAL SYNTHESIS OF CARAPANAUBINE [J].

FINCH, N ;

HSU, IHC ;

GEMENDEN, CW ;

TAYLOR, WI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (10) :1520-&

← 1 2 3 4 5 →