2002年7月
Asymmetric synthesis of (-)-adaline
ORGANIC LETTERS
- ,
- ,
- 巻
- 4
- 号
- 15
- 開始ページ
- 2469
- 終了ページ
- 2472
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1021/ol0200807
- 出版者・発行元
- AMER CHEMICAL SOC
[GRAPHIC]
An enantioselective total synthesis of (-)-adaline has been achieved starting from a chiral 6,6-disubstituted piperidone derivative previously prepared by diastereoselective allylation of a chiral tricyclic N-acyl-N,O-acetal. The key steps include lithium ion-activated S(N)2-type alkynylation of the tricyclic NO-acetal leading to exclusive formation of the (6S)-ethynylpiperidine and ring-closing olefin metathesis of the (2R,6S)-cis-2,6-dialkenylpiperidine for constructing the bridged azabicyclononane.
An enantioselective total synthesis of (-)-adaline has been achieved starting from a chiral 6,6-disubstituted piperidone derivative previously prepared by diastereoselective allylation of a chiral tricyclic N-acyl-N,O-acetal. The key steps include lithium ion-activated S(N)2-type alkynylation of the tricyclic NO-acetal leading to exclusive formation of the (6S)-ethynylpiperidine and ring-closing olefin metathesis of the (2R,6S)-cis-2,6-dialkenylpiperidine for constructing the bridged azabicyclononane.
- リンク情報
- ID情報
-
- DOI : 10.1021/ol0200807
- ISSN : 1523-7060
- Web of Science ID : WOS:000176938200006