66 ピラノナフトキノン抗生物質の新合成法

概要

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New Methods for the synthesis of Pyranonaphthoquinone anti-biotics are described. (1) Lewis acid mediated allylation of alkanoylquinones with allyltrimethylstannanes regioselectively occurs at the vicinal position of alkanoyl group to give the corresponding conjugate adducts in high yields. The allylic moiety is introduced to the quinone at the γ position of the corresponding allylstannans. (2) As new synthetic equivalent of 3-methoxycarbonylallyl anion, 1-methoxycarbonylallylsilanes (29) are prepared. The regioselective introduction of methoxycarbonyl group to allylsilane is accomplished by the nucleophilic addition to the "ate" complex (28) obtained from allyl anion and triethyl-aluminum. These methods are applied to the efficient synthesis of some typical pyranonaphthoquinones; eleuterin (1), isoeleuterin (2), deoxyfrenolicin(42), and nanaomycin A (5).
天然有機化合物討論会の論文
1981-09-10