Journal of the American Chemical Society p. 4368 - 4378 (1988)
Update date:2022-08-03
Topics: Column chromatography Catalyst Mass spectrometry Nucleophile Stereochemistry Total synthesis Reagent Protecting group Nuclear Magnetic Resonance (NMR) Chemical Synthesis
Danishefsky
Selnick
Zelle
DeNimo
The total synthesis of the title compound, which is a zinc-binding antibiotic, is described. The synthesis starts with aldehyde 4 and Grignard reagent 6. The key steps are (i) the cyclocondensation of aldehyde 10 with diene 11 under the influence of magnesium bromide, (ii) the cyclocondensation of aldehyde 24 with diene 33 under the influence of BF3·OEt2, (iii) the carbon Ferrier reaction of glycal acetate 37 with (E)-crotyltrimethylsilane, and (iv) the reductive merger of aldehyde 2a with sulfone 3.
View Morewebsite:http://www.cartoonchem.com/
Contact:+86-25-58074918
Address:Room 2109, RuiHua Business Center,315 South ZhongShan Road, Nanjing 210001, China
Chengdu Baishixing Science and Technology Industry Co., Ltd.
website:http://www.cd-bsx.com
Contact:+86-28-88531548
Address:#217,North of Industry Road,Heshan Town,Pujiang County,Chengdu,Sichuan,China.
website:http://www.vanzpharm.com/en/index.html
Contact:86-27-84492310
Address:FANHU INDUSTRY PARK
Tianjin Boron PharmaTech Co.,Ltd.(expird)
Contact:86-022-59845187
Address:B9-401, Tianda Science Park,No.80,4th Avenue,TEDA,Tianjin, China
Contact:+86-633-8332928
Address:No.1,Huanghai Yilu.Rizhao,Shandong
Doi:10.1016/j.bmc.2009.02.038
(2009)Doi:10.1016/S0040-4020(99)00554-2
(1999)Doi:10.1021/jo00312a004
(1990)Doi:10.1039/c0ob00903b
(2011)Doi:10.1021/jo701899j
(2007)Doi:10.1002/jlcr.1847
(2011)
