Bulletin of the Chemical Society of Japan p. 2483 - 2490 (1999)
Update date:2022-07-29
Topics:
Okumura, Kazuo
Suzuki, Taishi
Nakamura, Yutaka
Shin, Chung-gi
The first total synthesis of a macrocyclic antibiotic, micrococcin P1 (1), was achieved. This antibiotic has a unique structure and is constructed of four components called Fragments A, B, C, and D. In particular, the structures of the central pyridine skeleton (Fragment A) and the exocyclic side-chain (Fragment D) of 1 are slightly different from those of a similar antibiotic, micrococcin P (2). By various chemical modifications of the synthetic method for 2, the synthesis of the central 2,3,6-tris(substituted thiazolyl)pyridine segment [Fragment AC] 15 from ethyl 2-[6-dimethoxymethyl- 2-(1-ethoxyvinyl)-3-pyridyl]thiazole-4-carboxylate (9), followed by coupling of 15 with the Fragments B and D moieties synthesized independently, gave the protected Fragment A-B-C-D segment. Final intramolecular cyclization by using (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate as a condensing agent under high-dilution conditions and then deprotection of all the protecting groups with trifluoroacetic acid were effected successfully to give the expected synthetic 1.
View MoreNINGBO YINZHOU PRECISE COLOR CO.,LTD.
Contact:86-574-88139809 86-574-83033159
Address:Qiming Road,Yinzhou,Ningbo,China
Contact:+86-571-87010026
Address:202, Zhenhua Road,
Contact:86 21 3772 9386
Address:Rm.1803,Starry Bldg.1,1505 Meijiabang Road,Shanghai 201620 China
Zhengzhou Xinlian Chemical Tech Co. ,Ltd
Contact:0371-65771781 021-52042910
Address:H Part, Building I, No. 700 Gonglu Road, Pudong New Area, Shanghai
ANHUI CHEM-BRIGHT BIOENGINEERING CO.,LTD
Contact:86-561-4080321
Address:No.8 Lieshan Industrial Zone of Huaibei
Doi:10.1080/10426509608029655
(1996)Doi:10.1016/S0022-328X(98)00662-7
(1998)Doi:10.1021/jo062251h
(2007)Doi:10.1021/np9003189
(2009)Doi:10.1080/00268976200100461
(1962)Doi:10.1021/ol403290h
(2014)