A new synthesis of (−)-thioambrox and its 8-epimer

This new and straightforward synthesis of (−)-thioambrox 2 , a sulphur compound whose odour resembles ambergris, starts from sclareolide 4 . The stereoselectivity of the final cyclization is independent of the catalyst selected, and compound 2 is always favoured over (+)- iso-thioambrox 3 . With hyd...

Full description

Saved in:

Bibliographic Details
Published in:	Tetrahedron Vol. 61; no. 18; pp. 4403 - 4407
Main Authors:	Costa, Maria do Céu, Teixeira, Susana G., Rodrigues, Cristina B., Ryberg Figueiredo, Pedro, Marcelo Curto, Maria João
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 01-05-2005
Subjects:	iso-Thioambrox Stereoselective cyclization Thioambrox iso-Thioambrox Stereoselective cyclization Thioambrox
Online Access:	Get full text
Tags:	Add Tag No Tags, Be the first to tag this record!

Description
Summary:	This new and straightforward synthesis of (−)-thioambrox 2 , a sulphur compound whose odour resembles ambergris, starts from sclareolide 4 . The stereoselectivity of the final cyclization is independent of the catalyst selected, and compound 2 is always favoured over (+)- iso-thioambrox 3 . With hydrochloric acid as catalyst, the cyclization is unexpectedly stereospecific to give 2 in high yield at room temperature. Graphical Abstract
ISSN:	0040-4020 1464-5416
DOI:	10.1016/j.tet.2005.02.081