Stereoselective total synthesis of (±)-isocostic and (±)-3-oxoisocostic acids
Stereoselective total synthesis of the title compounds, two new sesquiterpenes isolated from a Mexican plant, are described. The key step in the synthesis is based on classical santon in syntheses by the stereoselective Michael addition of the potassium salt of ethyl α-cyanoacetate to the dienone(4), to give the cis adduct (5), in an 8 : 2 ratio with the trans isomer. Further appropriate transformation of this cis adduct (5) leads to formation of either isocostic acid (1) or 3-oxoisocostic acid (2).
1993 ◽
Vol 34
(17)
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pp. 2729-2732
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Keyword(s):
2016 ◽
Vol 12
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pp. 1096-1100
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2010 ◽
Vol 51
(7)
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pp. 1044-1047
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1990 ◽
Vol 68
(11)
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pp. 1917-1922
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Keyword(s):