Hyrtiosanes from Labdanes: (-)-Hyrtiosal from Sclareol

Pilar  Basabe; Alberto  Diego; David  Díez; Isidro S.  Marcos; Faustino  Mollinedo; Julio G.  Urones

doi:10.1055/s-2002-33332

PAPER

Hyrtiosanes from Labdanes: (-)-Hyrtiosal from Sclareol

Pilar Basabe*^a, Alberto Diego^a, David Díez^a, Isidro S. Marcos^a, Faustino Mollinedo^b, Julio G. Urones^a
^a Departimento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain
Fax: +34(923)294574; e-Mail: pbb@usal.es;
^b Centro de Investigación del Cáncer, CSIC-Universidad de Salamanca, Campus Miguel de Unamuno, 37007 Salamanca, Spain

Abstract

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Abstract

(-)-Hyrtiosal and its C-16 epimer have been prepared from sclareol in moderate yield. The absolute configuration of natural product (-)-hyrtiosal has being determined.

Key words

terpenoids - labdanes - hyrtiosal - sclareol - natural products - coupling - antitumor agents

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References

<A NAME="RE08601SS-1">1</A> Iguchi K. Shimada Y. Yamada Y. J. Org. Chem. 1992, 57: 522

<A NAME="RE08601SS-2">2</A> Basabe P. Diego A. Diez Martin D. Marcos IS. Urones JG. Synlett 2000, 1807

<A NAME="RE08601SS-3">3</A> Urones JG. Marcos IS. Basabe P. Gómez A. Estrella A. Lithgow AM. Nat. Prod. Lett. 1994, 5: 217

<A NAME="RE08601SS-4">4</A> Jean T. Heissler D. Synlett 1995, 607

<A NAME="RE08601SS-5">5</A> Ratcliffe R. Rodehost R. J. Org. Chem. 1970, 35: 4000

<A NAME="RE08601SS-6">6</A> Griffith WP. Ley SV. Withcombe GP. White AD. J. Chem. Soc., Chem. Commun. 1987, 1625

Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 145607. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223336033; e-mail: deposit@ccdc.cam.ac.uk.

<A NAME="RE08601SS-8">8</A> Paquette LA. Bulman-Page PC. Pansegrau PD. Wiedeman PE. J. Org. Chem. 1988, 53: 1450

<A NAME="RE08601SS-9A">9a</A> Bernardi R. Ghiringhelli D. J. Org. Chem. 1987, 52: 5021

<A NAME="RE08601SS-9B">9b</A> Lipshutz BH. Moretti R. Crow R. Tetrahedron Lett. 1989, 30: 15

<A NAME="RE08601SS-10">10</A> Stork G. Zhao K. Tetrahedron Lett. 1989, 30: 287