Terpenoid chemistryl: XXII. The trans, trans- and cis, cis-nepetalinic acids

Grant H.G. and Sutherland M.D. (1973) Terpenoid chemistryl: XXII. The trans, trans- and cis, cis-nepetalinic acids. Australian Journal of Chemistry, 26 10: 2183-2198. doi:10.1071/CH9732183


Author Grant H.G.
Sutherland M.D.
Title Terpenoid chemistryl: XXII. The trans, trans- and cis, cis-nepetalinic acids
Journal name Australian Journal of Chemistry   Check publisher's open access policy
ISSN 1445-0038
Publication date 1973-01-01
Sub-type Article (original research)
DOI 10.1071/CH9732183
Open Access Status
Volume 26
Issue 10
Start page 2183
End page 2198
Total pages 16
Subject 1600 Chemistry
Abstract A study of the trans, trans-nepetalinic acids has resolved the numerous discrepancies in the literature concerning the physical constants of these reference compounds and has correlated these properties and the stereochemistry of the two epimers. Thus (2S, 2‘S, 3‘S)-2(2'-carboxy-3'-methylcyclopentyl)propanoic acid shows m.p. 123.4-123.6°, [α]D -39° (1%, CHCl3+1% EtOH) and the (2R, 2‘S, 3‘S) epimer, m.p. 121.5-122°, [α]D -52° (1%, CHCl3+1% EtOH), or m.p. 142-143° for the (±)-acid. The cis, cis-nepetalinic acids have also been prepared and their stereochemistry assigned as (2S, 2‘R, 3‘S), m.p. 157-158°, [α]D +18.6° (1%, CHCl3+1% EtOH), and (2R, 2‘R, 3‘S), m.p. 68°, [α]D -36° (1%, CHCl3+1% EtOH).
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import - Archived
 
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Created: Tue, 04 Oct 2016, 12:39:10 EST by System User