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)
書誌事項
- タイトル別名
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- 9 Mangromicin A with Potent Antitrypanosomal Activity; Isolation, Structure Elucidation and Asymmetric Total Synthesis
抄録
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.
収録刊行物
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- 天然有機化合物討論会講演要旨集
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天然有機化合物討論会講演要旨集 59 (0), 49-54, 2017
天然有機化合物討論会実行委員会
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詳細情報 詳細情報について
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- CRID
- 1390004222620946176
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- NII論文ID
- 130007906363
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- ISSN
- 24331856
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可