45 四塩化チタンを用いる新しい合成反応 : 抗生物質Botryodiplodineの合成法

概要

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The new synthetic methods by the use of TiCl_4 were recently found (Figure 1〜Figure 8), and by utilyzing the above mentioned reaction, it was established that the antibiotic and anti-leukemic agent botryodiplodin is synthesized in good yield from cis-α-methyl-β-acetyl-γ-butyrolactone, produced by the reaction of α -methyl-α-angelicalactone with formaldehyde. Namely, the reaction of α-methyl-α-angelicalactone with formaldehyde in CH_2Cl_2 at 0℃ in the presence of BF_3・O(C_2H_5)_2, followed by quenching with NaHCO_3-saturated aqueous solution, resulted in the formation of corresponding α-methyl-β-acetyl-γ-butyrolactone in 92% yield. cis-product: trans-product=85:15. Thus, the stereoselectivity was observed in the present reaction. The present lactone synthesis was successfully applied to the synthesis of the antibiotic and anti-leukemic agent botryodiplodin. The synthetic conversions of the present method are outlined in Figure 12. We have therefore shown a convenient method for the synthesis of the antibiotic and anti-leukemic agent botryodiplodin.
天然有機化合物討論会の論文
1974-10-01