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Communication

Practical Synthesis and Diels−Alder Chemistry of [4]Dendralene

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Alan D. Payne, Anthony C. Willis,^† and Michael S. Sherburn*

Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia

J. Am. Chem. Soc., 2005, 127 (35), pp 12188–12189

DOI: 10.1021/ja053772+

Publication Date (Web): August 13, 2005

†

To whom correspondence should be addressed regarding crystal structures. E-mail: willis@rsc.anu.edu.au.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, sherburn@rsc.anu.edu.au

Abstract

Spectacular new atom efficient domino cycloaddition sequences involving [4]dendralene, the simplest cross-conjugated tetraene, are reported. Up to eight stereocenters, three new rings, and six C−C bonds are generated in one synthetic operation. The site selectivity of dienophile addition to cross-conjugated trienes and tetraenes is controlled with a simple Lewis acid.

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Published In Issue September 07, 2005
Received June 9, 2005

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Communication

Practical Synthesis and Diels−Alder Chemistry of [4]Dendralene

Abstract

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Cross-Coupling for Cross-Conjugation: Practical Synthesis and Diels−Alder Reactions of [3]Dendralenes

Cyclization of Cross-Conjugated Trienes: The Vinylogous Nazarov Reaction

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