51 (±)-Pseudodistomin AおよびBの合成研究(口頭発表の部)
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概要
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Pseudodistomins A and B (1a,2a), potent antineoplastic piperidine alkaloids with calmodulin antagonistic activity, were isolated from Okinawan tunicate Pseudodistoma kanoko as the first piperidine alkaloids from marine sources. For the establishment of their structures which have been deduced from the spectral data, we have investigated the total synthesis of pseudodistomins A and B and now succeeded in the first total synthesis of the proposed structures of their acetates. However, their proposed structures 1 and 2 were proved to be revised based on the results of our synthesis which has involved in two crucial photochemical reactions, reductive photocyclization of enamide and α-acylamino photoallylation. 1) Synthesis of the Proposed Structure of Pseudodistomin B Acetate Reductive photocyclization of enamide 7 with an oxazole ring followed by photoallylation of (methylthio)lactam 10 constructed 2,4,5-trisubstituted piperidone 13 with desired stereochemistry. Functionalization of ally group and removal of protective group gave the key intermediate 17 which was effectively used for the synthesis of 2b. Synthetic compound 2b was not identical with natural authentic sample. 2) Establishment of the Structure of Pseudodistomin B by the Total Synthesis of Its Acetate We proposed the structure 25 having a 6',8'-dienyl group in the alkenyl chain as pseudodistomin B and firmly established the structure by the total synthesis of its acetate from the key intermediate 17 via coupling reaction of C-C single bond. 3) On the Structure of Pseudodistomin A Proposing that pseudodistomin A is a regioisomer of pseudodistomin B, we are now undertaking the total synthesis of the acetate from the same key intermediate 17.
- 1992-09-10
著者
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内藤 猛章
神戸女薬大
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木口 敏子
神戸女薬大
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木口 敏子
神戸薬大
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祐本 葉子
神戸女薬大
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内藤 猛章
神戸女子薬科大学
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二宮 一彌
神戸女薬大
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二宮 一弥
神戸薬大
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二宮 一彌
Kobe Women's College Of Pharmacy
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内藤 猛章
神戸薬科大学
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