Journal of Organic Chemistry p. 321 - 330 (1995)
Update date:2022-08-02
Topics:
Deroose, Frederik D.
De Clercq, Pierre J.
Two conceptually attractive enantioselective syntheses of (+)-biotin from L-cysteine are reported based upon an intramolecular 1,3-dipolar cycloaddition of a carbamoyl azide.The first approach (12 steps) involves the following as key-steps: (i) the macrothiolactonization of acid 10b to Z-olefin 14, (ii) the thermolysis of the ene carbamoyl azide 15 in water with direct formation of a mixture of the benzylated derivatives of (+)-biotin 16a and 17a.The second approach (14 steps) involves the following: (i) elimination of bromide 29 to the endocyclic thioenol ether 30, (ii) thermolysis of the ene carbamoyl azide 30 to the exocyclic thioenol ethers 31a and 31b.Both the synthesis of 29 and the final transformation of 31a and 31b into (+)-biotin are based upon literature precedents.
View MoreQuzhou Ruiyuan chemical Co., Ltd
Contact:+86-570-3039321/3039361/3039308
Address:18# Huayang Road,Quzhou High-tech Industrial Park, Zhejiang China.
Reliable Pharma Technology (Shanghai) Co., Ltd.
Contact:0086-21-67676847-8008
Address:Lane 1500, No.68, Xinfei Road, Songjiang District, Shanghai, 201611, P.R.China.
SHANDONG AONA CHEMICAL CO.,LTD.
Contact:86-532-85762926
Address:LIUYUAN TOWN, ZAOZHUANG CITY, SHANGDONG PROVINCE.
Contact:+852-8198 2399
Address:9E, Leapont Industrial Building, 18-28 Wo Liu Hang Road, Shatin, New Territories, Hong Kong
Valiant Fine Chemicals Co., Ltd.
Contact:+86 535 6101878/6374484
Address:11 Wuzhishan Rd.,YTETDZ,Yantai,264006,Shandong,China
Doi:10.1016/j.tet.2020.131064
(2020)Doi:10.1002/hlca.200590262
(2005)Doi:10.1023/A:1016238110533
(1995)Doi:10.1021/acs.jmedchem.6b00541
(2016)Doi:10.1055/s-2006-950276
(2006)Doi:10.1021/jo800367r
(2008)