Asymmetric synthesis of ABC tricyclic core in Daphniphyllum alkaloid 21-deoxy-macropodumine D

被引：17

作者：

Mo, Xiu-Fang ^{[1
]}

Li, Yun-Fei ^{[1
]}

Sun, Ming-Hui ^{[1
]}

Dong, Qiu-Yan ^{[1
]}

Xie, Qin-Xia ^{[1
]}

Tang, Pei ^{[1
]}

Xue, Fei ^{[2
,3
]}

Qin, Yong ^{[2
,3
]}

机构：

[1] Chongqing Univ, Sch Pharmaceut Sci, Chongqing Key Lab Nat Prod Synth & Drug Res, Chongqing 401331, Peoples R China

[2] Sichuan Univ, Sichuan Engn Lab Plant Sourced Drug, West China Sch Pharm, Chengdu 610041, Sichuan, Peoples R China

[3] Sichuan Univ, West China Sch Pharm, Res Ctr Drug Ind Technol, Chengdu 610041, Sichuan, Peoples R China

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 21期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

Daphniphyllum alkaloid; 21-Deoxymacropodumine D; Asymmetric conjugate addition; Aza-Michael addition; Pd-catalyzed alpha-alkenylation; A-TYPE ALKALOIDS; BIOMIMETIC TOTAL-SYNTHESIS; TETRACYCLIC CORE; RING-SYSTEM; EXPEDIENT CONSTRUCTION; (-)-CALYCIPHYLLINE N; RADICAL CYCLIZATIONS; RAPID CONSTRUCTION; CALYCIPHYLLINE; DAPHENYLLINE;

D O I：

10.1016/j.tetlet.2018.04.019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper, we describe our efforts toward the asymmetric synthesis of Daphniphyllum alkaloid 21-deoxymacropodumine D which led to efficient preparation of a ABC tricyclic framework containing five consecutive stereocenters. This synthetic work features (1) utilization of an asymmetric conjugate addition to install the C5 all-carbon quaternary center, (2) an intramolecular aza-Michael addition followed by Pd-catalyzed alpha-alkenylation to build the bowl-shaped tricyclic core. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：1999 / 2004

页数：6

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