TY - JOUR
T1 - A Synthesis of Podocarpic Acid
AU - Spencer, Thomas A.
AU - Friary, Richard J.
AU - Schmiegel, Walter W.
AU - Simeone, Joseph F.
AU - Watt, David S.
PY - 1968
Y1 - 1968
N2 - Reductive carbomethoxylation of α,β-unsaturated ketone 4 was investigated as a potential route to intermediates, such as keto ester 2, with the podocarpic acid (3) stereochemistry. However, none of the desired 12 and only a low yield of isomeric 15 was obtained. Intermediate 2 was prepared instead from 12 isolated from methylation of 8. Other products from this methylation and several related bicyclic terpenoid substances, such as triols 29 and 30, are described. Methyl dl-podocarpate (40) was synthesized from 2 via Robinson annelation in 13% over-all yield.
AB - Reductive carbomethoxylation of α,β-unsaturated ketone 4 was investigated as a potential route to intermediates, such as keto ester 2, with the podocarpic acid (3) stereochemistry. However, none of the desired 12 and only a low yield of isomeric 15 was obtained. Intermediate 2 was prepared instead from 12 isolated from methylation of 8. Other products from this methylation and several related bicyclic terpenoid substances, such as triols 29 and 30, are described. Methyl dl-podocarpate (40) was synthesized from 2 via Robinson annelation in 13% over-all yield.
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U2 - 10.1021/jo01266a050
DO - 10.1021/jo01266a050
M3 - Article
AN - SCOPUS:0010848586
SN - 0022-3263
VL - 33
SP - 719
EP - 726
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -