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SYNTHESIS AND SYNTHESIS-BASED STRUCTURAL ELUCIDATION OF (-)-MACROSPHELIDES J AND K
- An, Hongchan;
- Kim, Seung-Hee;
- Kim, Heegyu;
- Kim, Kyeojin;
- Sim, Jaehoon;
- ... Paek, Seung-Mann;
- 외 3명
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2초록
The structures of (-)-macrosphelides J and K have been elucidated via asymmetric total syntheses. Key points of the structure elucidation include an initial prediction of the stereochemistries of (-)-macrosphelides J and K based on the structural relationship of the macrosphelides and molecular modeling of macrosphelide B. Our synthetic approach features an isoxazoline-based route involving a diastereoselective olefin-nitrile oxide cycloaddition, an intricate reductive N-O bond cleavage of an isoxazoline and O-alkylation of the labile beta-hydroxy ketone intermediate.
키워드
Macrosphelides J and K; Structural Prediction and Elucidation; Molecular Modeling; Olefin-Nitrile Oxide Cycloaddition; Biosynthetic Pathway; CELL-ADHESION INHIBITORS; ORALLY BIOAVAILABLE INHIBITORS; MACROSPHELIDE-E-G; NATURAL-PRODUCTS; ABSOLUTE STEREOSTRUCTURES; ISOXAZOLINE ROUTE; ENANTIOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; ARTIFICIAL MACROSPHELIDES; CHEMOSELECTIVE METHOD
- 제목
- SYNTHESIS AND SYNTHESIS-BASED STRUCTURAL ELUCIDATION OF (-)-MACROSPHELIDES J AND K
- 저자
- An, Hongchan; Kim, Seung-Hee; Kim, Heegyu; Kim, Kyeojin; Sim, Jaehoon; Jang, Jaebong; Paek, Seung-Mann; Suh, Young-Ger; Yun, Hwayoung
- 발행일
- 2015-05-01
- 유형
- Article
- 저널명
- Heterocycles
- 권
- 91
- 호
- 5
- 페이지
- 970 ~ 988