Journal of Organic Chemistry p. 4412 - 4418 (1995)
Update date:2022-08-03
Topics:
Roush
Coffey
A synthesis of ketone 4, corresponding to the fully elaborated naphthoquinone nucleus of awamycin, is described. The synthesis involves the Diels-Alder reaction between diene 8 and quinone 9 to construct naphthoquinone 10, the coupling of bromide 15 and an ansa chain surrogate 17 via an aryllithium intermediate, and a late stage 1,4-addition of NaSMe to naphthoquinone 23 to afford the ketone 4.
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