11 (+)-Pederinの全合成

概要

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(+)-Pederin (1) is a potent insect poison isolated from Paederus fuscipes. The unique stereostructure of 1 having nine chiral centers has attracted the attention of synthetic organic chemists. We recently reported the stereoselective reduction of acyclic ketones with Zn(BH_4)_2 and the general methods for the syntheses of both 1,3-syn- and 1,3-anti-polyols. We now report the total synthesis of (+)-pederin (1) based on these newly developed methods. 1) Stereoselective Synthesis of (+)-Benzoylselenopederic Acid (+)-Benzoylselenopederic acid (4), the left half of pederin, was synthesized stereoselectively using Zn(BH_4)_2 reduction twice. 2) Stereoselective Synthesis of (+)-Benzoylpedamide (+)-Benzoylpedamide (5), the right half of pederin, was synthesized under virtually complete stereoselection using the method for the synthesis of 1,3-syn- and 1,3-anti-polyols effectively. 3) Total Synthesis of (+)-Pederin (+)-Pederin (1) was synthesized via the coupling of the left half 4 and the right half 5, followed by the NaBH_4 reduction.
天然有機化合物討論会の論文
1985-09-07