2002年8月
First total syntheses of the phytotoxins solanapyrones D and E via the domino Michael protocol
JOURNAL OF ORGANIC CHEMISTRY
- 巻
- 67
- 号
- 17
- 開始ページ
- 5969
- 終了ページ
- 5976
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1021/jo0163602
- 出版者・発行元
- AMER CHEMICAL SOC
The phytotoxins solanapyrones D (1) and E (2) have been synthesized from the decalone prepared by the domino Michael reaction of the kinetic enolate of optically pure acetylcyclohexene with methyl crotonate. The decalone was transformed into a solanapyrone core by equilibration into thermodynamically stable trans-decalone (11), dehydroxylation, and dehydration. Condensation of a methyl acetoacetate equivalent followed by cyclization installed a pyrone moiety. Introduction of a formyl or hydroxymethyl unit into the pyrone ring via Pummerer related reactions furnished solanapyrones D (1) and E (2).
- リンク情報
-
- DOI
- https://doi.org/10.1021/jo0163602
- CiNii Articles
- http://ci.nii.ac.jp/naid/80015501629
- PubMed
- https://www.ncbi.nlm.nih.gov/pubmed/12182630
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000177559800017&DestApp=WOS_CPL
- ID情報
-
- DOI : 10.1021/jo0163602
- ISSN : 0022-3263
- CiNii Articles ID : 80015501629
- PubMed ID : 12182630
- Web of Science ID : WOS:000177559800017