Journal of the Chemical Society. Perkin transactions I p. 2481 - 2486 (1990)
Update date:2022-08-05
Topics:
Shishido, Kozo
Tokunaga, Yuji
Omachi, Naomi
Hiroya, Kou
Fukumoto, Keiichiro
Kametani, Tetsuji
The enantioselective total syntheses of the drimane-type sesquiterpenes albicanol (1) and albicanyl acetate (2) starting from (+)-Wieland-Miescher ketone (8) have been accomplished.The key step in the synthetic strategy involves a highly diastereoselective intramolecular <3+2> dipolar cycloaddition reaction of th nitrile oxide (6), which affords the isoxazoline (5) as the sole product in high yield.Reductive hydrolysis of compound (5) followed by methylenation of the resulting β-hydroxy ketone (4) by application of the Nozaki-Lombardo procedure provides (+)-albicanol (1), which is then converted into (+)-albicanyl acetate (2) by acetylation.The olefinic acetal (15), an intermediate of the present total synthesis, has been transformed by sequential Jones oxidation and methylation into a secosesquiterpene (17), one of the components of sun-cured Greek tabacco.
View MoreContact:+86-22-83718541
Address:32th Floor, Rongqiao Center Intersection of Changjiang Road and Nankai Six Road Nankai District Tianjin 300102, China
Chengdu Biopurify Phytochemicals Ltd.
website:http://www.phytopurify.com
Contact:+86-28-82633397
Address:2F,No.11 Building,No.388 Rongtaidadao CNSTP,Wenjiang Zone,Chengdu,Sichuan, China
Shanghai Science Peptide Biological Technology Co.,ltd
website:http://www.scipeptide.com
Contact:+86-21-51099675
Address:No.8 Changyang Rd
Shijiazhuang City Xiehe Pharmaceutical Co., Ltd
Contact:+86-311-80817929
Address:Shangzhuang,Shijiazhuang,China
Shanghai agrotree chemical co.,ltd.
Contact:+86-21-50117563
Address:Room 8A,liangfeng building,No.8 dongfang RD.pudong,shanghai,China
Doi:10.1002/chem.201000284
(2010)Doi:10.1002/chem.201505016
(2016)Doi:10.1021/acs.nanolett.6b04827
(2017)Doi:10.3184/030823410X520741
(2010)Doi:10.1016/S0040-4020(01)81323-5
(1989)Doi:10.1016/j.bmcl.2010.08.021
(2010)
