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The synthesis of dl-sandaracopimaradiene, dl-pimaradiene and some observations on the structure of rimuene

✍ Scribed by Robert E. Ireland; Peter W. Schiess

Publisher
Elsevier Science
Year
1960
Tongue
French
Weight
272 KB
Volume
1
Category
Article
ISSN
0040-4039

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✦ Synopsis

In the field of total synthesis of the dlterpenoid resin acids, efforts reported to date have concerned themselves with construction of the appropriate A and B rings 2. We now wish to report the results of a program directed toward the elaboration of the ring C substitution pattern present in the pimaric acids.

~Wnen the tricyclic ketone(I), prepared independently in substantially the same fashion as that reported by Turner and co-workers 3, was condensed with ethyl formate in the presence of sodium methoxide and then with pyrrolidine, there resulted an 83% yield of the pyrrolidinomethylene ketone(II, R=C4H8N ) A portion of this work was presented at the International Symposium on The Chemistry of Natural Products, Sydney, Australia, August, 1960.

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