Tetrahedron p. 4798 - 4812 (2016)
Update date:2022-08-16
Topics:
Monta?a, ángel M.
Barcia, Joan
Corominas, Albert
Pyranic hemiaminal synthons are present in natural and unnatural products with biological activity. Here a synthetic pathway to prepare this type of intermediates is presented. The methodology is based on three main steps: a) The [4+3] cycloaddition reaction of an α,α'-dihaloketone and a conveniently protected 2-aminofuran diene. b) Chemical modification of the resulting oxabicyclic cycloadduct and orthogonal protection of organic functions, and c) Reductive ozonolysis of the C6–C7 double bond of the modified cycloadduct to afford a pentasubstituted polyfunctionalized pyranic hemiaminal ester with up to 94% yield. When working with 2,4-dibromo-3-pentanone and 2-tert-butoxycarbonylaminofuran as starting materials, the C32–C38 subunit of immunosuppressant sanglifehrin A was obtained with excellent yield.
View MorePenglai Qianwei Chemical Co., Ltd.
Contact:86-535-3357802
Address:Shahelu (north), Penglai, Shandong, China
Shaanxi HuaTai Bio-fine chemical company Ltd
Contact:86-029-87862197
Address:No. 5, 3rd Floor, 29 Yanta North Road, Beilin Dist.
Hangzhou Sartort Biopharma Co., Ltd
website:http://www.sartort.com
Contact:86-571-87039693
Address:No. 57, Tech Park Road, Hangzhou, Zhejiang, China
Dongying J&M Chemical Co., Ltd,
Contact:546-8551108
Address:Room 1219, Zisheng Mansion, Zibo Road, Dongying, Shandong, China
Contact:+86-21-6856-1349 523-87676172
Address:No16 . BinJiang Road . Taixing Economy Developing Area .JiangSu Province . China
Doi:10.1007/BF03187274
(1953)Doi:10.1038/224511a0
(1969)Doi:10.1016/0022-1902(72)80089-7
(1972)Doi:10.1016/S1872-2067(18)63069-4
(2018)Doi:10.1016/S0045-6535(00)00242-3
(2001)Doi:10.1021/acs.chemmater.7b02533
(2017)