A New Formal Total Synthesis of β-Elemenone

References

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• 1980 . Rev. Soc. Quím. Méx. , 24 : 226 This work was first presented by L. A. Maldonado in the XV Congreso Mexicano de Química Pura y Aplicada, Acapulco, Gro., México (October 1980). See, resume ORG 14
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• With MeMgI in ether mixtures of tertiary alcohol 7 and ketone 6 were produced, which can be separated by column chromatography (SiO2). Ketone 6 is a pale yellow oil; ir (film) v 1720 cm−1; pmr (CDCl3) δ 5.85 (s, 1 olefinic hydrogen), 3.40 (s, S-CH2CH2 -S), 3.05 (t, J = 5 Hz, allylic CH α to the ketone), 2.20 (s, CH 3-C=0) and 1.65 (s, CH 3-C=CH)
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• With SOCl2 in pyridine a complex mixture was obtained from which we could isolate and purify in low yield the rearranged compound 10
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• Other reagents tested in this conversion were : 1) MeI in refluxing aqueous MeCN or aqueous DMF (recovered starting material) and 2) Ce(NH4)2 (NO3)6 in aqueous MeCN (30–59% yield of 9)
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• In one experiment a 50% yield of 2 was obtained but yields were usually in the range of 20–30%. The balance of material were unidentified alcohol products and some starting material
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• We thank Professor P.A. Grieco for sending us spectra of compound 2 (September 1979)
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