Total synthesis of the antimycoplasma antibiotic micacocidin

被引：39

作者：

Ino, A ^{[1
]}

Hasegawa, Y ^{[1
]}

Murabayashi, A ^{[1
]}

机构：

[1] Shionogi & Co Ltd, Aburahi Labs, Shiga 5203423, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 21期

关键词：

antibiotics; thiazolines; thiazolidines; chelation;

D O I：

10.1016/S0040-4039(98)00518-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of the antimycoplasma antibiotic micacocidin (1) is described. Construction of sterically hindered thiazoline 12 was achieved by a phosphorus pentachloride-mediated cyclization reaction of S-protected aryloylcysteine 11, and compound 1 with desired chirality at C-10 was favorably obtained from diastereomeric mixture 30 through formation of the Zn complex 31. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3509 / 3512

页数：4

共 20 条

[1]

Shionogi & Co., Ltd. Patent, WO 96/04262

[2]

Kobayashi, S., Hidaka, S., Kawamura, Y., Ozaki, M., Hayase, Y., J. Antibiotics, , in press

[3]

Kobayashi, S., Nakai, H., Ikenishi, Y., Sun, W.Y., Ozaki, M., Takeda, R., Hayase, Y., J. Antibiotics, , in press

[4]

note

[5]

Cox, C.D., Rinehart Jr., K.L., Moore, M.L., Cook Jr., J.C., (1981) Proc. Natl. Acad. Sci. U.S.A., 78, pp. 4256-4260

[6]

Ankenbauer, R.G., Toyokuni, T., Staley, A., Rinehart Jr., K.L., Cox, C.D., (1988) J. Bacteriol., 170, pp. 5344-5351

[7]

Drechsel, H., Stephan, H., Lotz, R., Haag, H., Zahner, H., Hantke, K., Jung, G., (1995) Liebigs Ann., pp. 1727-1733

[8]

Kubo, I., Kim, M., Naya, K., Komatsu, S., Yamagiwa, Y., Ohashi, K., Sakamoto, Y., Kamikawa, T., (1987) Chem. Lett., pp. 1101-1104

[9]

note

[10]

note

← 1 2 →