Journal of the Chemical Society. Perkin transactions I p. 2747 - 2756 (1995)
Update date:2022-07-30
Topics:
Jones, David W.
Lock, Christopher J.
Dehydration of the formyl acid 3 (R = H) with acetic anhydride in benzene at 80 deg C generates the quinonoid pyrone 4 which can be trapped with norbornadiene, N-phenylmaleimide and enol silyl ethers; the adduct 6 (R = Me, P = TES) and its 9-epimer 10 from 2-(triethylsilyloxy)propene are readily transformed into (+/-)-auramycinone 2 (R = Me) whilst those <6 (R = vinyl, P = TES) and its 9-epimer> from 2-(triethylsilyloxy)buta-1,3-diene are readily converted into the methyl ethers 24, 25, 33 and 34 of which 24, 33 and 34 are known to be readily converted into (+/-)-aklavinone 2 (R = Et).
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