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Synthesis 2010(13): 2179-2200  
DOI: 10.1055/s-0029-1220007
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Cyclopentadienylcobalt-Mediated Intermolecular Cycloaddition of α,ω-Diynes to (Cyclo)alkenes: Synthesis of Linearly Fused Oligocycles and Extension to Enantiomerically Pure (6aR,10aR)-Dihydroanthracyclinones

Corinne Auberta, Vincent Gandonb, Sangdon Hanc, Barry M. Johnsonc, Max Malacriaa, Sten Schömenauerc, K. Peter C. Vollhardt*c, Glenn D. Whitenerc
a UPMC Université Paris 06, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), 4 place Jussieu, C. 229, 75005 Paris, France
b Université Paris-Sud, UMR CNRS 8182, 91405 Orsay, France
c Department of Chemistry, University of California at Berkeley, Berkeley, California 94720-1460, USA
Fax: +1(510)6435208; e-Mail: kpcv@berkeley.edu;
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Publication History

Received 26 March 2010
Publication Date:
18 May 2010 (online)

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Abstract

The generality of the [CpCoL2]-mediated [2+2+2] cycloaddition of α,ω-diynes to (cyclo)alkenes has been extended to include linear oligocycles as models for the one-step, A + D → ABCD construction of optically pure, novel 6,10-dihydroanthracyclinones.

Key words

alkenes - alkynes - cycloadditions - polycycles - transition metals

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