Tandem intramolecular Diels-Alder (TIMDA) reactions: Branched substrate studies and new synthetic pathways

Article abstract of DOI:10.1080/00397919508011386

Using a malonic ester route, the first branched tandem intramolecular Diels-Alder (TIMDA) precursor, 3, was synthesized from sorbic acid in seven steps (15% overall yield). Treatment with Lewis acid catalysts (e.g., boron trifluoride etherate) affects the TIMDA reaction to afford a new fused-tetracyclic, 4, as two diastereomers (1:1). An alternative synthetic route to key intermediates used in the synthesis of linear TIMDA precursors has also been achieved.

Full text of DOI:10.1080/00397919508011386

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Synthetic Communications: An
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Organic Chemistry
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Tandem Intramolecular Diels-
Alder (Timda) Reactions:
Branched Substrate Studies and
New Synthetic Pathways
Michael A. Brodney a , Justin P. O'Leary a , Jeffrey A.
Hansen a & Raymond J. Giguere a
a Department of Chemistry, Skidmore College,
Saratoga Springs, NY, 12866-1632, USA
Published online: 23 Sep 2006.
To cite this article: Michael A. Brodney , Justin P. O'Leary , Jeffrey A. Hansen &
Raymond J. Giguere (1995) Tandem Intramolecular Diels-Alder (Timda) Reactions:
Branched Substrate Studies and New Synthetic Pathways, Synthetic Communications:
An International Journal for Rapid Communication of Synthetic Organic Chemistry,
25:4, 521-531, DOI: 10.1080/00397919508011386
To link to this article: http://dx.doi.org/10.1080/00397919508011386
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