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 Aubert; Vincent Gandon; Sangdon Han; Barry M. Johnson; Max Malacria; Sten Schömenauer; K. Peter C. Vollhardt; Glenn D. Whitener

doi:10.1055/s-0029-1220007

PAPER

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 Aubert^a, Vincent Gandon^b, Sangdon Han^c, Barry M. Johnson^c, Max Malacria^a, Sten Schömenauer^c, K. Peter C. Vollhardt*^c, Glenn D. Whitener^c
^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;

Abstract

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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

Volltext

Referenzen

References

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X-ray structures:

19a

For compound 54, an X-ray structure was determined by Professor Ling-Kang Liu of the National Taiwan University, Taiwan, in 1987, and a cif file could not be generated. For structure tables and coordinates, please contact the primary author.

19b

CCDC 770347 and CCDC 770348 contain the supplementary crystallographic data for 66 and 67, respectively. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

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