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Extension of the Tandem Conjugate Addition−Dieckmann Condensation:  The Formal Synthesis of Tetracenomycin A2

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journal contribution
posted on 20.02.2004, 00:00 authored by Denis V. Kozhinov, Victor Behar
Tandem cuprate addition−Dieckmann condensation is featured in the construction of the polyketide metabolite tetracenomycin A2 (2). Thus, cyclization substrate 11 was treated with Gilman cuprate Me2CuLi to afford anthracene 12. The phenolic acetate protecting group of 12 ensured its chemoselective oxidation to reveal terminal quinone 13, which intercepts the previously reported synthesis of tetracenomycin A2 (2).