- Synthesis of (+/-)-aklavinone and (+/-)-auramycinone via electrondeficient o-quinonoid pyrones
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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 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).
- Jones, David W.,Lock, Christopher J.
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p. 2747 - 2756
(2007/10/02)
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- SYNTHESES OF (+/-)-AKLAVINONES. APPLICATION OF THE STEREOCONTROLLED "ZIPPER" BICYCLO-CYCLIZATION REACTION
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Efficient syntheses of (+/-)-aklavinones; (+/-)-aklavinone (1), (+/-)-auramycinone (2), and (+/-)-13-methylaklavinone (3), are described.A key process of the tetracyclic ring construction in these syntheses is a stereocontrolled "zipper" bicyclo-cyclizati
- Uno, Hidemitsu,Naruta, Yoshinori,Maruyama, Kazuhiro
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p. 4725 - 4742
(2007/10/02)
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