Issue 19, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Enantiospecific syntheses of pseudopterosin aglycones. Part 1. Synthesis of the putative aglycone of pseudopterosin G–J via an A→AB→ABC annulation strategy

Robert Chow,a   Philip J. Kocienski,*a   Alexander Kuhl,b   Jean-Yves LeBrazidec,b   Kenneth Muirb  and  Paul Fishc  

* Corresponding authors

a Department of Chemistry, Leeds University, Leeds, UK

b Department of Chemistry, Glasgow University, Glasgow, UK

c Pfizer Central Research, Sandwich, Kent, UK

Abstract

The putative aglycone of pseudopterosin G–J and its enantiomer were synthesised enantiospecifically from 2,3-dimethoxytoluene and η3-allyl cationic complexes of molybdenum and iron respectively. The A→AB→ABC annulation strategy entailed the use of allyl cations or their equivalents for the creation of the three benzylic stereogenic centres. The X-ray structure of tetrahydronaphthalene (−)-41a was determined

Graphical abstract: Enantiospecific syntheses of pseudopterosin aglycones. Part 1. Synthesis of the putative aglycone of pseudopterosin G–J via an A→AB→ABC annulation strategy

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Article information

DOI
https://doi.org/10.1039/B102960F
Article type
Paper
Submitted
02 Apr 2001
Accepted
27 Jul 2001
First published
07 Sep 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 2344-2355

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Enantiospecific syntheses of pseudopterosin aglycones. Part 1. Synthesis of the putative aglycone of pseudopterosin G–J via an A→AB→ABC annulation strategy

R. Chow, P. J. Kocienski, A. Kuhl, J. LeBrazidec, K. Muir and P. Fish, J. Chem. Soc., Perkin Trans. 1, 2001, 2344 DOI: 10.1039/B102960F

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