Total Syntheses of Highly Oxidized ent-Kaurenoids Pharicin A, Pharicinin B, 7-O-Acetylpseurata C, and Pseurata C: A [5+2] Cascade Approach

被引：92

作者：

He, Chi ^{[1
]}

Hu, Jialei ^{[1
]}

Wu, Yubing ^{[1
]}

Ding, Hanfeng ^{[1
,2
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310058, Zhejiang, Peoples R China

[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 17期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; KAURANE DITERPENOIDS; (-)-MAOECRYSTAL V; H FUNCTIONALIZATION; RADICAL CYCLIZATION; ORGANIC-SYNTHESIS; SINGLET OXYGEN; MAOECRYSTAL V; ROUTE; PHYLLOCLADENE;

D O I：

10.1021/jacs.7b02746

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The unprecedented oxidative dearomatization-induced [5+2] cycloaddition/pinacol-type 1,2-acyl migration cascade efficiently generates a quaternary carbon center and assembles the highly oxygenated bicyclo[3.2.1]octane framework of ent-kaurene diterpenoids. By incorporation of the subsequent retro-aldol/aldol process and singlet oxygen ene reaction, this concise and convergent approach has enabled the first asymmetric total syntheses of pharicin A, pharicinin B, 7-O-acetylpseurata C, and pseurata C.

引用

页码：6098 / 6101

页数：4

共 53 条

[41] Diterpenoids from Isodon species and their biological activities [J].

Sun, Han-Dong ;

Huang, Sheng-Xiong ;

Han, Quan-Bin .

NATURAL PRODUCT REPORTS, 2006, 23 (05) :673-698

[42]

TANABE M, 1967, TETRAHEDRON LETT, P3943

[43] TOTAL SYNTHESIS OF PHYLLOCLADENE [J].

TURNER, RB ;

GANSHIRT, KH ;

SHAW, PE ;

TAUBER, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (08) :1776-&

[44] SINGLET OXYGEN IN ORGANIC-SYNTHESIS [J].

WASSERMAN, HH ;

IVES, JL .

TETRAHEDRON, 1981, 37 (10) :1825-1852

[45] Pharicin A, a novel natural ent-kaurene diterpenoid, induces mitotic arrest and mitotic catastrophe of cancer cells by interfering with BubR1 function [J].

Xu, Han-Zhang ;

Huang, Ying ;

Wu, Ying-Li ;

Zhao, Yong ;

Xiao, Wei-Lie ;

Lin, Qi-Shan ;

Sun, Han-Dong ;

Dai, Wei ;

Chen, Guo-Qiang .

CELL CYCLE, 2010, 9 (14) :2897-2907

[46] A Unified Strategy to ent-Kauranoid Natural Products: Total Syntheses of (-)-Trichorabdal A and (-)-Longikaurin E [J].

Yeoman, John T. S. ;

Mak, Victor W. ;

Reisman, Sarah E. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (32) :11764-11767

[47] [5+2] Cycloaddition Reactions in Organic and Natural Product Synthesis [J].

Ylijoki, Kai E. O. ;

Stryker, Jeffrey M. .

CHEMICAL REVIEWS, 2013, 113 (03) :2244-2266

[48] Convergent Route to ent-Kaurane Diterpenoids: Total Synthesis of Lungshengenin D and 1α,6α-Diacetoxy-ent-kaura-9(11),16-dien12,15-dione [J].

Zhao, Xiangbo ;

Li, Wu ;

Wang, Junjie ;

Ma, Dawei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (08) :2932-2935

[49] ent-Kaurane Diterpenoids from Isodon pharicus [J].

Zhao, Yong ;

Pu, Jian-Xin ;

Huang, Sheng-Xiong ;

Ding, Li-Sheng ;

Wu, Ying-Li ;

Li, Xian ;

Yang, Li-Bin ;

Xiao, Wei-Lie ;

Chen, Guo-Qiang ;

Sun, Han-Dong .

JOURNAL OF NATURAL PRODUCTS, 2009, 72 (06) :988-993

[50] Diterpenoids from Isodon pharicus [J].

Zhao, Yong ;

Huang, Sheng-Xiong ;

Xiao, Wei-Lie ;

Ding, Li-Sheng ;

Pu, Jian-Xin ;

Li, Xian ;

Yang, Li-Bin ;

Sun, Han-Dong .

TETRAHEDRON LETTERS, 2009, 50 (17) :2019-2023

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