天然有機化合物討論会講演要旨集
Online ISSN : 2433-1856
第59回天然有機化合物討論会実行委員会
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9 抗トリパノソーマ活性を有するマングロマイシン類の単離、構造決定ならびに不斉全合成 (口頭発表の部)
*廣瀬 友靖中島 琢自高田 拓和岩月 正人山田 健落合 純也神谷 義之石原 拓真長井 賢一郎松本 厚子石山 亜紀乙黒 一彦塩見 和朗高橋 洋子砂塚 敏明大村 智
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会議録・要旨集 オープンアクセス

p. 49-54

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Two new cyclopentadecane antibiotics, named mangromicins A and B, were separated out from the culture broth of Lechevalieria aerocolonigenes K10-0216. The chemical structures of the two novel compounds were elucidated by instrumental analyses, including various NMR, MS and X-ray crystallography. Mangromicins A and B consist of cyclopentadecane skeletons with a tetrahydrofuran unit and a 5,6-dihydro-4-hydroxy-2-pyrone moiety. Mangromicins A and B showed in vitro antitrypanosomal activity with IC50 values of 2.4 and 43.4 μg/ml, respectively. An enantioselective total synthesis of (+)-mangromicin A has also been accomplished. The tetrahydrofuran ring of mangromicin A, possessing a tetrasubstituted carbon center, was constructed by Mukaiyama-type vinylogous alkylation via a cyclic oxocarbenium intermediate derived from a γ-hydroxy ketone with ideal stereoselectivity, and the 4-hydroxydihydropyrone scaffold was generated via Dieckmann condensation at a late stage of the total synthesis. The reliable asymmetric synthesis of (+)-mangromicin A has revealed the absolute configuration of naturally occurring mangromicin A.

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