Journal of the Chemical Society. Perkin transactions I p. 705 - 713 (1996)
Update date:2022-08-03
Topics:
Jones, David W.
Nongrum, Firstborn Matthew
Unlike o-quinodimethanes lacking a bridge between the termini of the diene system e.g. 18a (n = 3 or 4), the 2-benzopyran-3-ones 10a, 10b and 10c undergo endo-selective intramolecular Diels-Alder addition of the connecting chain to give cis-BC fused ring systems of type 13. The adduct 13b is converted into the ester 21 with methanolic HCl and into the ketol 36 by LiAlH4 reduction followed by oxidation (MnO2). The ketone 31 is prepared from 21 by epoxidation followed by BF3·Et2O-catalysed rearrangement; with NaOMe-CD3OD it fails to undergo cis-trans isomerisation and fails to incorporate deuterium at C-8 probably due to the overwhelming acidity of the C-6 protons. The cis-dihydronaphthalene 26 obtained from 21 gives cis-21 with KOBut-(CD3)2SO showing the greater thermodynamic stability of the cis-fused ring system in this case.
View MoreHangzhou Eastbiopharm Co.,Ltd.
Contact:+86-571-88931780
Address:Hangzhou,China
Taixing Shenfeng Chemical Co., Ltd.
Contact:+86-523-87117033, 87117666
Address:4# Yinsanlu, Huangqiao town, Taixing, Jiangsu, China.
Shandong Yubin Chemical CO.,LTD
website:http://www.yukaichem.com/en.html
Contact:+86-536-8865336
Address:binhai economic development zone，262737 shangdong，china
Shanghai Science Peptide Biological Technology Co.,ltd
website:http://www.scipeptide.com
Contact:+86-21-51099675
Address:No.8 Changyang Rd
Huludao Tianqi Shengye Chemical Co.,Ltd.
Contact:0086 429 2075777
Address:Area B,Shipbuilding Industry Park,Beigang District,Huludao City,Liaoning prov.,China
Doi:10.1016/S0040-4039(01)82475-8
(1974)Doi:10.1002/anie.200390132
(2003)Doi:10.1021/ja01858a049
(1940)Doi:10.1039/c1jm11154j
(2011)Doi:10.1021/ja01321a037
(1934)Doi:10.1021/ja01161a092
(1950)
