
TY  - JOUR
A1  - Grant, HG 
A1  - Sutherland, MD 
T1  - Terpenoid chemistry. XXII. The <I>trans,trans</I>- and <I>cis,cis</I>-nepetalinic acids
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1973
VL  - 26
IS  - 10
SP  - 2183
EP  - 2198
KW  - 
UR  - https://doi.org/10.1071/CH9732183 
N2  - 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°, [&#945;]D -39° (1%, CHCl3+1% EtOH) and the (2R,2?S,3?S) epimer, m.p. 121.5-122°, [&#945;]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°, [&#945;]D +18.6° (1%, CHCl3+1% EtOH), and (2R,2?R,3?S), m.p. 68°, [&#945;]D -36° (1%, CHCl3+1% EtOH). 
ER  -

