Journal of the Chemical Society. Perkin transactions I p. 579 - 584 (1992)
Update date:2022-08-02
Topics:
Brimble, Margaret A.
Nairn, Michael R.
A synthesis of pyranonaphthoquinone-spiroacetal 12 is reported which represents an efficient entry to the pentacyclic framework of the pyranonaphthoquinone antibiotic griseusin A.The key step involves assembly of the furo<3,2-b>naphtho<2,3-d>pyran 11 via a ceric ammonium nitrate oxidative rearrangement of the furo<3,2b>naphtho<2,1-d>furan 10.This latter heterocycle 10 in turn was constructed via the uncatalysed 1,4-addition of 2-trimethylsilyloxyfuran 9 to naphthoquinone 8.Naphthoquinone 8 is readily available from 1,4-dimethoxynaphthalene-2-carbaldehyde 3 and acetylene 4.
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