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The absolute configuration of (-)-homostachydrine from alfalfa

✍ Scribed by H. C. Beyerman

Book ID
104586012
Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
334 KB
Volume
78
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

Recently Wiehler and Marion isolated from the seeds of alfalfa (Medicago sativa) the laevo‐rotatory methyl betaine of hexahydropyridine‐2‐carboxylic acid, for which they suggested the name of (‐)‐homostachydrine.

This compound has now been prepared from L‐(‐)‐hexahydropyridine‐2‐carboxylic acid (L‐(‐)‐pipecolic acid). (‐)‐Homostachydrine therefore possesses the L‐configuration.

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The ab8olute configuration of homolaoflavanonts isolated from Ru8carf 8pecias was determinsd by applying the chiral excfton coupling method to suitable derivatives. A negative Cotton effect In the 287-295 nm region of the CD curve8 of the natural compounds 1118 8hom to bs indicative of 3R-configurat