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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 19
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Original Articles

Degradation of the Side Chain of (−)‐Sclareol: A Very Short Synthesis of nor‐Ambreinolide and Ambrox

A. F. Barrero Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071, Granada, Spain
,
E. J. Alvarez‐Manzaneda Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071, Granada, SpainCorrespondence[email protected]
,
R. Chahboun Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071, Granada, Spain
&
A. F. Arteaga Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071, Granada, Spain
Pages 3631-3643 | Received 29 Jul 2003, Published online: 10 Jan 2011
 
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Abstract

The synthesis of nor‐Ambreinolide (8) from (‐)‐sclareol (1) was carried out by treatment with KMnO4‐Ac2O and further alkaline hydrolysis. 8 was directly transformed into (‐)‐ambrox (11) by reduction with metal borohydride in the presence of Lewis acids.

Acknowledgments

We should like to thank the CICYT (Projet 1FD97‐1103) for financial support.

Notes

*These assignments may be interchanged.

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