Journal of the Chemical Society. Perkin transactions I p. 2027 - 2048 (1987)
Update date:2022-08-03
Topics:
Battersby, Alan R.
Baker, Mark G.
Broadbent, Hugo A.
Fookes, Christopher J. R.
Leeper, Finian J.
Syntheses are described of three 2H-pyrroles (pyrrolenines), (15), (28), and (64), which were designed to test the chemical feasibility of the rearrangements proposed as part of the mechanism of the enzyme cosynthetase (uroporphynogen III synthase).All three syntheses create the 2H-pyrrole ring by the Michael addition of nitronate anion to an α,β-unsaturated ester and one introduces an additional substituent by novel alkylations of the dianion of a hydroxamic acid.Some of intermediates in the syntheses showed unusual n.m.r. properties which reveal strong conformational preferences.The rearrangement of the 2H-pyrroles was studied under both thermal and acid-catalysed conditions.The results show that 2,2-disubstituted 2H-pyrroles only rearrange easily by <1,5>-sigmatropic shifts if they do not have further substituents on C-3 and C-4. 2-Pyrrolylmethyl-2H-pyrroles prefer to rearrange by a fragmentation-recombination mechanism.
View MoreMTT Pharma & Bio-technology Co.,Ltd(expird)
Contact:+86-21-58407925
Address:Room2019, Building C, Tomson Center, No.158, Zhang Yang Road, Shanghai, China
Allright GC (Jinan) Biotechnology Ltd.
website:https://www.argcbiotech.com/
Contact:86-18405413579-
Address: No.27566 of Jingshiroad, Huaiyin District, Jinan City(250011), Shandong Province, China.
Jiangsu Hualun Chemical Industry Co., Ltd
website:http://www.hualunchem.com
Contact:+86-0514-86464168 86507985
Address:39# Middle Renmin Road, Dinghuo Town
guide(suzhou) fine materials co. ltd
Contact:0512-80972173
Address:21st Building, No.369 Lushan Rd, New District Suzhou China 215129
Contact:86-571-87758773
Address:Room604 ,6F, Block A1-3 Xixi Plaza,No. 588 Wenyi West RD, Hangzhou,310012, China
Doi:10.1039/DT9880000617
(1988)Doi:10.1016/S0040-4039(00)96584-5
(1987)Doi:10.1016/S0040-4020(01)90295-9
(1987)Doi:10.1007/s11173-005-0132-0
(2005)Doi:10.1002/jhet.5570450405
(2008)Doi:10.1021/ja00238a017
(1987)
