Agricultural and Biological Chemistry
Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369
Synthesis of Streptovitacin-C2 Isomers
Sachio KUDOTakayuki ORITANIKyohei YAMASHITA
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1985 Volume 49 Issue 10 Pages 2919-2923

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Abstract

(2R*, 4S*, 6S*, αS*)- and (2R, 4R, 6R, αS)-Streptovitacin-C2 (STV-C2) (1a and 1b) were synthesized by an aldol condensation of (2R*, 4S*)- or (2R, 4R)-2, 4-dimethyl-2-trimethylsiloxy-1-cyclohexanone (15a or 15b) with 4-(2-oxoethyi)-2, 6-piperidinedione (16), which was followed by desilylation of the products. The stereochemistry of the synthesized STV-C2 isomers (1a and 1b) was elucidated by NMR. STV-C2 isomers (1a and 1b) did not show strong antimicrobial activity against Saccharomyces cerevisiae and Pyricularia oryzae.

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