37 ホスラクトマイシンBとホストリエシンの合成(口頭発表の部)

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Phoslactomycin B and fostriecin are a unique class of compounds possessing a phosphate group and, in the latte molecule, an amino group. A similarity between these two molecules suggests the same strategy will be applicable to synthesis of these molecules. Recently, we have studied synthesis of fostriecin and established a strategy using chelation-contolled addition of a vinyl anion to an α-PMB-oxy ketone and metathesis for construction of the central part and the lactone moiety of fostriecin, respectively (Org. Lett. 2002, 4, 4615). We then applied the strategy to synthesis of phoslactomycin B. Chelation controlled addition proceeded efficiently, while the lactone formation by metathesis proceeded little. Furthermore, diimine reduction of the iodo-acetylene gave a mixture of the desired product, the over-reduction product, and the recovered compound. We then studied another construction of the lactone ring through Evans aldol reaction followed by Wittig reaction and lactonization, which produced the lactone efficiently. On the other hand, Sonogashira coupling of the acetylene end with 2-cyclohexyl-1-iodoethene took place cleanly to produce the conjugated enyne efficiently. Latter, this moiety was reduced to the conjugated diene with activated Zinc. The amino group was introduced as (allyl-OCO)_2N and the phosphonate group was introduced as (allyl-O)_2P(O) group. In the last stage, these groups were removed by using Bu_3SnH and Pd catalyst to afford phoslactomycin B (Angew. Chem. Int. Ed. 2006, 45, 3320). In a similar way, deamino phoslactomycin B, a proposed intermediate in the biosynthesis of phoslactonycin B, was synthesized efficiently.
天然有機化合物討論会の論文
2006-09-15

37 ホスラクトマイシンBとホストリエシンの合成(口頭発表の部)

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