Sequential [3 + 2] and [4 + 2] cycloadditions for stereoselective synthesis of a novel polyheterocyclic scaffold

Qing Lu; Xin Huang; Gonghua Song; Chung-Ming Sun; Jerry P. Jasinski; Amanda C. Keeley; Wei Zhang

doi:10.1021/co400026s

Sequential [3 + 2] and [4 + 2] cycloadditions for stereoselective synthesis of a novel polyheterocyclic scaffold

Qing Lu
, Xin Huang
, Gonghua Song
, Chung-Ming Sun
, Jerry P. Jasinski
, Amanda C. Keeley
, Wei Zhang^*

^*此作品的通信作者

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研究成果: Article › 同行評審

29 引文斯高帕斯（Scopus）

摘要

A strategy of combining [3 + 2] cycloaddition and intramolecular Diels-Alder reaction is developed for the synthesis of a novel polycyclic scaffold with skeletal and substitutional diversities. Intermediates generated from stereoselective [3 + 2] cycloaddition of azomethine ylides and maleimides were derivatized for intramolecular Diels-Alder reaction of furan to form highly condensed heterocyclic products as racemic single diastereomers.

原文	English
頁（從 - 到）	350-355
頁數	6
期刊	ACS Combinatorial Science
卷	15
發行號	7
DOIs	https://doi.org/10.1021/co400026s
出版狀態	Published - 8 7月 2013

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10.1021/co400026s

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title = "Sequential [3 + 2] and [4 + 2] cycloadditions for stereoselective synthesis of a novel polyheterocyclic scaffold",

abstract = "A strategy of combining [3 + 2] cycloaddition and intramolecular Diels-Alder reaction is developed for the synthesis of a novel polycyclic scaffold with skeletal and substitutional diversities. Intermediates generated from stereoselective [3 + 2] cycloaddition of azomethine ylides and maleimides were derivatized for intramolecular Diels-Alder reaction of furan to form highly condensed heterocyclic products as racemic single diastereomers.",

keywords = "[3 + 2] cycloaddition, intramolecular Diels-Alder reaction, polyheterocyclic scaffold, sequential cycloadditions, stereoselective annulation",

author = "Qing Lu and Xin Huang and Gonghua Song and Chung-Ming Sun and Jasinski, \{Jerry P.\} and Keeley, \{Amanda C.\} and Wei Zhang",

year = "2013",

month = jul,

day = "8",

doi = "10.1021/co400026s",

language = "English",

volume = "15",

pages = "350--355",

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T1 - Sequential [3 + 2] and [4 + 2] cycloadditions for stereoselective synthesis of a novel polyheterocyclic scaffold

AU - Lu, Qing

AU - Huang, Xin

AU - Song, Gonghua

AU - Sun, Chung-Ming

AU - Jasinski, Jerry P.

AU - Keeley, Amanda C.

AU - Zhang, Wei

PY - 2013/7/8

Y1 - 2013/7/8

N2 - A strategy of combining [3 + 2] cycloaddition and intramolecular Diels-Alder reaction is developed for the synthesis of a novel polycyclic scaffold with skeletal and substitutional diversities. Intermediates generated from stereoselective [3 + 2] cycloaddition of azomethine ylides and maleimides were derivatized for intramolecular Diels-Alder reaction of furan to form highly condensed heterocyclic products as racemic single diastereomers.

AB - A strategy of combining [3 + 2] cycloaddition and intramolecular Diels-Alder reaction is developed for the synthesis of a novel polycyclic scaffold with skeletal and substitutional diversities. Intermediates generated from stereoselective [3 + 2] cycloaddition of azomethine ylides and maleimides were derivatized for intramolecular Diels-Alder reaction of furan to form highly condensed heterocyclic products as racemic single diastereomers.

KW - [3 + 2] cycloaddition

KW - intramolecular Diels-Alder reaction

KW - polyheterocyclic scaffold

KW - sequential cycloadditions

KW - stereoselective annulation

UR - https://www.scopus.com/pages/publications/84879944473

U2 - 10.1021/co400026s

DO - 10.1021/co400026s

M3 - Article

C2 - 23701651

AN - SCOPUS:84879944473

SN - 2156-8952

VL - 15

SP - 350

EP - 355

JO - ACS Combinatorial Science

JF - ACS Combinatorial Science

IS - 7

ER -

Sequential [3 + 2] and [4 + 2] cycloadditions for stereoselective synthesis of a novel polyheterocyclic scaffold

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