Issue 13, 2003
From the journal:

Organic & Biomolecular Chemistry

Synthesis of differentially protected/functionalised acetylenic building blocks from p-benzoquinone and their use in the synthesis of new enediynes†

Sethuraman Sankararaman*a  and  Manivannan Srinivasana  

* Corresponding authors

a Department of Chemistry, Indian Institute of Technology Madras, Chennai – 600 036, India
E-mail: sanka@iitm.ac.in
Fax: 91 44 22570545
Tel: 91 44 22578252

Abstract

Sequential addition of two different lithium acetylides to p-benzoquinone yielded diastereomeric mixtures of 1,4-diethynylcyclohexa-2,5-diene-1,4-diols wherein the two ethynyl groups bear different protective/functional groups. Selective deprotection to the terminal acetylene followed by Pd(0) mediated coupling with Z-1,2-dichloroethene yielded new enediynes bearing cyclohexa-2,5-diene units.

Graphical abstract: Synthesis of differentially protected/functionalised acetylenic building blocks from p-benzoquinone and their use in the synthesis of new enediynes

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Article information

DOI
https://doi.org/10.1039/B302323K
Article type
Paper
Submitted
03 Mar 2003
Accepted
20 May 2003
First published
04 Jun 2003

Org. Biomol. Chem., 2003,1, 2388-2392

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Synthesis of differentially protected/functionalised acetylenic building blocks from p-benzoquinone and their use in the synthesis of new enediynes

S. Sankararaman and M. Srinivasan, Org. Biomol. Chem., 2003, 1, 2388 DOI: 10.1039/B302323K

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