2021年6月
Asymmetric total synthesis of (-)-javaberine A and (-)-epi-javaberine A based on catalytic intramolecular hydroamination of N-methyl-2-(2-styrylaryl)ethylamine
TETRAHEDRON
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- 巻
- 90
- 号
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1016/j.tet.2021.132165
- 出版者・発行元
- PERGAMON-ELSEVIER SCIENCE LTD
Asymmetric total synthesis of (-)-javaberine A and its epimer was achieved by utilizing two methods for isoquinoline synthesis, asymmetric hydroamination of N-methyl-2-(2-styrylaryl)ethylamine and Bischler-Napieralski cyclization. Intramolecular asymmetric hydroamination of N-methyl aminoalkene 4 was catalyzed by lithium amide-chiral bisoxazoline to give tetrahydroisoquinoline (S)-laudanosine with good enantioselectivity in excellent yield. N-Demethylation of (S)-laudanosine was accomplished by Polonovski-type reaction to give (S)-norlaudanosine. Condensation of (S)-norlaudanosine with homoveratric acid, and subsequent Bischler-Napieralski cyclization, LiAlH4 reduction, and O-demethylation furnished (8R,14S)-(-)-javaberine A, corresponding to antipode of natural javaberine A. (8S,14S)-(-)-Javaberine A, which corresponds to C14-epimer of natural javaberine A, was also successfully synthesized. (C) 2021 Elsevier Ltd. All rights reserved.
- リンク情報
- ID情報
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- DOI : 10.1016/j.tet.2021.132165
- ISSN : 0040-4020
- eISSN : 1464-5416
- Web of Science ID : WOS:000663120400002