Synthesis of clitocine, a new insecticidal nucleoside from the mushroom Clitocybe inversa

…, S Fujie, Y Yamagiwa, M Kim, H Kawaguchi

Index: Kamikawa, Tadao; Fujie, Satoru; Yamagiwa, Yoshiro; Kim, Mujo; Kawaguchi, Hitoshi Journal of the Chemical Society, Chemical Communications, 1988 , # 3 p. 195 - 196

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Citation Number: 18

Abstract

Scheme 1. Reagentsand conditions: i,(3), Et, N, DMF, room temp.; ii, NH3, MeOH, 0 C; iii,(6), Et3N, DMF, room temp.; iv, CF, C02HH20 (9: l), room temp., 6 min. 19% yield. Treatment of (4) with ammonia-saturated methanol at room temperature gave clitocine in 72% yield. The physical properties (tlc, hplc, and nmr) were identical with those of natural clitocine. However, the inefficiency and lack of reproducibility of the condensation step [probably ...