
TY  - JOUR
A1  - Bannon, CD 
A1  - Eade, RA 
A1  - James, P 
A1  - McKenzie, GP 
A1  - Simes, JJH 
T1  - Extractives of Australian timbers. XII. Minor sapogenins of <I>Castanospermum australe</I> (Leguminosae). A stereospecific synthesis of methyl 2&#946;,3&#946;-Dihydroxyolean-12-en-28-oate
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1973
VL  - 26
IS  - 3
SP  - 629
EP  - 639
KW  - 
UR  - https://doi.org/10.1071/CH9730629 
N2  - The sapogenin mixture prepared from the extract of the wood of Castanospermum australe Cunn. &amp; Fras. has been shown to contain the known triterpenes 2&#946;,3&#946;-dihydroxyolean-12-en-28-oic acid and 3&#946;- hydroxyolean-12-ene-23,28-dioic acid; the latter also occurs as the free triterpene. The identity of methyl 2&#946;,3&#946;-dihydroxyolean-12-en-28- oic acid has been established by a high yielding stereospecific synthesis starting from methyl crategolate; this synthesis at the same time confirmed the revised configurations assigned from N.M.R. evidence1 to the hydroxy groups in the two cis-2,3-diols of the isomeric methyl 2,3-dihydroxyolean-12-en-28-oates. The identity of methyl 3&#946;- hydroxyolean-12-ene-23,28-dioate has been established by comparison with a specimen prepared by an unambiguous synthesis from dimethyl medicagenate. 
ER  -

