Literature DB >> 16468721

Synthesis of the erythrina alkaloid 3-demethoxyerythratidinone. Novel acid-induced rearrangements of its precursors.

Qiu Wang1, Albert Padwa.   

Abstract

[reaction: see text] A new strategy for the synthesis of 3-demethoxyerythratidinone has been developed and is based on an extraordinarily facile intramolecular Diels-Alder reaction of a 2-imido-substituted furan. During the course of the synthesis, several novel acid-induced rearrangement reactions were encountered.

Entities:  

Mesh：

Substances：

Year:  2006        PMID： 16468721      PMCID： PMC2495026          DOI： 10.1021/ol0527330

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  17 in total

1.  Conformational study of the intramolecular diels-alder reaction of a pentadienyl acrylate. Theoretical evaluation of kinetic and thermodynamic control

Authors: 
Journal:  Org Lett       Date:  2000-10-19       Impact factor: 6.005

2.  The total synthesis of (+/-)-pumiliotoxin-C.

Authors:  W Oppolzer; W Fröstl
Journal:  Helv Chim Acta       Date:  1975-03-12       Impact factor: 2.164

3.  Origins of stereoselectivity in intramolecular Diels-Alder cycloadditions of dienes and dienophiles linked by ester and amide tethers.

Authors:  D J Tantillo; K N Houk; M E Jung
Journal:  J Org Chem       Date:  2001-03-23       Impact factor: 4.354

4.  Sequential aminodiene Diels-Alder approach to the ergoline skeleton.

Authors:  Albert Padwa; Scott K Bur; Hongjun Zhang
Journal:  J Org Chem       Date:  2005-08-19       Impact factor: 4.354

5.  Syntheses of pyrrolo- and indoloisoquinolinones by intramolecular cyclizations of 1-(2-arylethyl)-5-benzotriazolylpyrrolidin-2-ones and 3-benzotriazolyl-2-(2-arylethyl)-1-isoindolinones.

Authors:  A R Katritzky; S Mehta; H Y He
Journal:  J Org Chem       Date:  2001-01-12       Impact factor: 4.354

6.  Rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with phenols

Authors: 
Journal:  Org Lett       Date:  2000-06-15       Impact factor: 6.005

7.  Cycloaddition-Rearrangement Sequence of 2-Amido Substituted Furans as a Method of Synthesizing Hexahydroindolinones.

Authors:  Albert Padwa; Michael A. Brodney; Kyosuke Satake; Christopher S. Straub
Journal:  J Org Chem       Date:  1999-06-25       Impact factor: 4.354

8.  Stereoselectivity of superacid-catalyzed Pictet-Spengler cyclization reactions.

Authors:  Satoshi Nakamura; Masaru Tanaka; Tooru Taniguchi; Masanobu Uchiyama; Tomohiko Ohwada
Journal:  Org Lett       Date:  2003-06-12       Impact factor: 6.005

9.  Total synthesis of (+/-)-stenine using the IMDAF cycloaddition of a 2-methylthio-5-amido-substituted furan.

Authors:  John D Ginn; Albert Padwa
Journal:  Org Lett       Date:  2002-05-02       Impact factor: 6.005

10.  Rh(I)-catalyzed ring opening of an IMDAF-derived oxabicyclo cycloadduct as the key step in the synthesis of (+/-)-epi-zephyranthine.

Authors:  Qiu Wang; Albert Padwa
Journal:  Org Lett       Date:  2004-06-24       Impact factor: 6.005
View more
  7 in total

1.  Acid-promoted cyclization reactions of tetrahydroindolinones. Model studies for possible application in a synthesis of selaginoidine.

Authors:  Mickea D Rose; Michael P Cassidy; Paitoon Rashatasakhon; Albert Padwa
Journal:  J Org Chem       Date:  2007-01-19       Impact factor: 4.354

2.  Concise synthesis of the Erythrina alkaloid 3-demethoxyerythratidinone via combined rhodium catalysis.

Authors:  Jung Min Joo; Ramoncito A David; Yu Yuan; Chulbom Lee
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

3.  Application of the aza-Achmatowicz oxidative rearrangement for the stereoselective synthesis of the Cassia and Prosopis alkaloid family.

Authors:  Carolyn A Leverett; Michael P Cassidy; Albert Padwa
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

4.  Protic-solvent-mediated cycloisomerization of quinoline and isoquinoline propargylic alcohols: syntheses of (±)-3-demethoxyerythratidinone and (±)-cocculidine.

Authors:  Stephen T Heller; Toshihiro Kiho; Alison R H Narayan; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-05       Impact factor: 15.336

5.  Synthesis of the tetracyclic framework of the erythrina alkaloids using a [4 + 2]-cycloaddition/Rh(I)-catalyzed cascade of 2-imidofurans.

Authors:  Albert Padwa; Qiu Wang
Journal:  J Org Chem       Date:  2006-09-15       Impact factor: 4.354

6.  Synthesis of some members of the hydroxylated phenanthridone subclass of the Amaryllidaceae alkaloid family.

Authors:  Albert Padwa; Hongjun Zhang
Journal:  J Org Chem       Date:  2007-03-06       Impact factor: 4.354

7.  A Short Synthesis of (±)-3-Demethoxyerythratidinone by Ligand-Controlled Selective Heck Cyclization of Equilibrating Enamines.

Authors:  Emma E Blackham; Kevin I Booker-Milburn
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-04       Impact factor: 15.336
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.