Literature DB >> 16292831

An efficient synthesis of coumestrol and coumestans by iodocyclization and Pd-catalyzed intramolecular lactonization.

Tuanli Yao1, Dawei Yue, Richard C Larock.   

Abstract

[reaction: see text] The iodocyclization of acetoxy-containing 2-(1-alkynyl)anisoles and subsequent direct palladium-catalyzed carbonylation/lactonization provide an efficient route to naturally occurring coumestan and coumestrol, and their related analogues.

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Year:  2005        PMID： 16292831     DOI： 10.1021/jo0517038

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  12 in total

1.  Synthesis of 3-sulfenyl- and 3-selenylindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal alkynes, followed by n-Bu(4)NI-induced electrophilic cyclization.

Authors:  Yu Chen; Chul-Hee Cho; Feng Shi; Richard C Larock
Journal:  J Org Chem       Date:  2009-09-04       Impact factor: 4.354

2.  Highly substituted lactone/ester-containing furan library by the palladium-catalyzed carbonylation of hydroxyl-substituted 3-iodofurans.

Authors:  Chul-Hee Cho; Richard C Larock
Journal:  ACS Comb Sci       Date:  2011-03-24       Impact factor: 3.784

3.  Iodine/palladium approaches to the synthesis of polyheterocyclic compounds.

Authors:  Saurabh Mehta; Richard C Larock
Journal:  J Org Chem       Date:  2010-03-05       Impact factor: 4.354

4.  Synthesis of Psoralidin derivatives and their anticancer activity: First synthesis of Lespeflorin I1.

Authors:  Pallab Pahari; Ujwal Pratim Saikia; Trinath Prasad Das; Chendil Damodaran; Jurgen Rohr
Journal:  Tetrahedron       Date:  2016-06-09       Impact factor: 2.457

5.  A novel synthetic route to 3-sulfenyl- and 3-selenylindoles by n-Bu4NI-induced electrophilic cyclization.

Authors:  Yu Chen; Chul-Hee Cho; Richard C Larock
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

6.  Competition studies in alkyne electrophilic cyclization reactions.

Authors:  Saurabh Mehta; Jesse P Waldo; Richard C Larock
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

7.  A simple and mild synthesis of 1H-isochromenes and (Z)-1-alkylidene-1,3-dihydroisobenzofurans by the iodocyclization of 2-(1-alkynyl)benzylic alcohols.

Authors:  Raffaella Mancuso; Saurabh Mehta; Bartolo Gabriele; Giuseppe Salerno; William S Jenks; Richard C Larock
Journal:  J Org Chem       Date:  2010-02-05       Impact factor: 4.354

8.  Skeletal diversification via heteroatom linkage control: preparation of bicyclic and spirocyclic scaffolds from N-substituted homopropargyl alcohols.

Authors:  Thomas O Painter; Jonathon R Bunn; Frank J Schoenen; Justin T Douglas; Victor W Day; Conrad Santini
Journal:  J Org Chem       Date:  2013-04-01       Impact factor: 4.354

9.  Total synthesis of psoralidin, an anticancer natural product.

Authors:  Pallab Pahari; Jürgen Rohr
Journal:  J Org Chem       Date:  2009-04-03       Impact factor: 4.354

10.  Tuneable access to indole, indolone, and cinnoline derivatives from a common 1,4-diketone Michael acceptor.

Authors:  Dalel El-Marrouki; Sabrina Touchet; Abderrahmen Abdelli; Hédi M'Rabet; Mohamed Lotfi Efrit; Philippe C Gros
Journal:  Beilstein J Org Chem       Date:  2020-07-17       Impact factor: 2.883
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