Pentacyclic Furanosteroids: The Synthesis of Potential Kinase Inhibitors Related to Viridin and Wortmannolone

被引：21

作者：

Lang, Yunhui ^{[1
]}

Souza, Fabio E. S. ^{[1
]}

Xu, Xinshe ^{[1
]}

Taylor, Nicholas J. ^{[1
]}

Assoud, Abdeljalil ^{[1
]}

Rodrigo, Russell ^{[1
]}

机构：

[1] Univ Waterloo, Dept Chem, Waterloo, ON N2L 3G1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 15期

基金：

加拿大自然科学与工程研究理事会;

关键词：

DIELS-ALDER REACTIONS; PHOSPHOINOSITIDE; 3-KINASE; RING-SYSTEM; CYCLOADDITIONS; ALKALOIDS; CHEMISTRY;

D O I：

10.1021/jo900922q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regiocontrolled intermolecular Diels-Alder reaction of all o-benzoquinone followed by all intramolecular nitrile oxide cyclization is employed to prepare the BCD fragment of viridin. The AE segment is attached to it by means of an intramolecular Diels-Alder reaction of an o-benzoquinone monoketal generated in situ from tricycle 15 and 5-trimethylsilyl-2E,4E-pentadienol 20. The silyl substituent at C-1 of the pentacyclic product directs the dihydroxylation of the C-2-C-3 double bond to its beta-face. Various transformations of the 1-trimethylsilyi-2 beta,3 beta-dihydroxy pentacycle into several others with oxygen substituents in ring A are described. One of these products 40 possesses the same structure and relative stereochemistry in rings A, B, and E as that of the natural product wortmannolone 3.

引用

页码：5429 / 5439

页数：11

共 50 条

[1] Strategies for the Total Synthesis of the Furanosteroids: wortmannin and viridin
Xue, Dongsheng
He, Haibing
Gao, Shuanhu
CHEMISTRY LETTERS, 2021, 50 (03) : 497 - 502
[2] Toward the total synthesis of Viridin class of furanosteroids
Jacobi, Peter A.
Onyango, Evans O.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
[3] Total synthesis of furanosteroids natural products: Viridin and nodulisporiviridin E
Ji, Yang
Gao, Shuanhu
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
[4] Studies on the synthesis of furanosteroids. I. viridin models
Sessions, E. Hampton
Jacobi, Peter A.
ORGANIC LETTERS, 2006, 8 (18) : 4125 - 4128
[5] Viridin-based PI-3 kinase inhibitors
Wipf, Peter
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
[6] Design and Combinatorial Synthesis of a Library of Methylenesulfonamides and Related Compounds as Potential Kinase Inhibitors
Torr, Jane E.
Large, Jonathan M.
McDonald, Edward
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2009, 12 (03) : 275 - 284
[7] Progress towards viridin:: synthesis of the pentacyclic furanosteroid ring system via o-benzoquinonoid cycloadditions
Souza, FES
Rodrigo, R
CHEMICAL COMMUNICATIONS, 1999, (19) : 1947 - 1948
[8] Synthesis, biological evaluation and in silico investigations of benzotriazole derivatives as potential inhibitors of NIMA related kinase
Qadri, Tahir
Aziz, Mubashir
Channar, Pervaiz Ali
Ejaz, Syeda Abida
Hussain, Mumtaz
Attaullah, Hafiz Muhammad
Ujan, Rabail
Hussain, Zahid
Zehra, Tasneem
Saeed, Aamer
Shah, M. R.
Ogaly, Hanan A.
Al-Zahrani, Fatimah A. M.
RSC ADVANCES, 2023, 13 (48) : 33826 - 33843
[9] Design, synthesis and therapeutic potential of adenosine kinase inhibitors.
Erion, MD
Ugarkar, B
Boyer, S
Gomez, J
Dumas, D
Rosengren, S
Firestein, G
Wiesner, JB
Foster, AC
Gruber, H
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 247 - MEDI
[10] Synthesis of indazolones and pthalimides as potential cyclin dependent kinase inhibitors
Miles, Veronica
Joseph, Faith
Pham, Nancy
Schroeder, Richard
Iqbal, Mariya
Sridhar, Jayalakshmi
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251

← 1 2 3 4 5 →