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Synthesis 2001(11): 1619-1622
DOI: 10.1055/s-2001-16750
PAPER
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of Saturated 14-Membered Ring γ-Hydroxy Macrolides

Leena Kaisalo*, Tapio Hase
Department of Chemistry, Laboratory of Organic Chemistry, University of Helsinki, P.O.Box 55, FIN-00014 University of Helsinki, Finland
Fax: +358(9)19150366; e-Mail: leena.kaisalo@helsinki.fi;
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Publication History

Received 10 January 2001
Publication Date:
28 September 2004 (online)

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Abstract

Stereoselective synthesis of two diastereomers of a saturated 14-membered γ-hydroxy macrolide using conformational stereocontrol is reported.

Key words

macrocycles - lactones - macrolides - diastereoselectivity - conformational stereocontrol

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7

The diastereomeric ratio of the acetylated products was determined by GC.

9

The calculations of 4 should be considered as approximate because some of the force field (MM3*) parameters were low quality parameters. We did the calculations also in an MM2* force field but many of the obtained low energy conformations violated the Schweizer-Dunitz rule. [11]

12

Structural assignments of products 5 and 6 are based on the differences in the 1H NMR shifts and coupling constants of the starting materials 7 and 9 [3] and on the X-ray structure of 9.