SYNTHESIS OF (+ -)-AKLAVINONE AND (+/-)-AURAMYCINONE VIA ELECTRON-DEFICIENT O-QUINONOID PYRONES/

Authors
JONES DW LOCK CJ
Citation
Dw. Jones et Cj. Lock, SYNTHESIS OF (+ -)-AKLAVINONE AND (+/-)-AURAMYCINONE VIA ELECTRON-DEFICIENT O-QUINONOID PYRONES/, Journal of the Chemical Society. Perkin transactions. I, (21), 1995, pp. 2747-2755
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
21
Year of publication
1995
Pages
2747 - 2755
Database
ISI
SICI code
0300-922X(1995):21<2747:SO(-A(>2.0.ZU;2-G
Abstract
Dehydration of the formyl acid 3 (R = H) with acetic anhydride in benz ene at 80 degrees C generates the quinonoid pyrone 4 which can be trap ped with norbornadiene, N-phenylmaleimide and enol silyl ethers; the a dduct 6 (R = Me, P = TES) and its 9-epimer 10 from 2-(triethylsilyloxy )propene are readily transformed into (+/-)-auramycinone 2 (R = Me) wh ilst those [6 (R =vinyl, P = TES) and its 9-epimer] from 2(triethylsil yloxy)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 converte d into (+/-)-aklavinone 2 (R = Et).