(+)-Zwittermicin A. Rapid assembly of C9-C15 and a formal total synthesis.
作者： Evan W. Rogers , Tadeusz F. Molinski
DOI: 10.1021/JO901007V
关键词: Epoxide 、 Total synthesis 、 Chemistry 、 Desymmetrization 、 Enantiomer 、 Enantioselective synthesis 、 Stereochemistry 、 Sharpless epoxidation 、 Chemical synthesis 、 Azide
摘要: A short, enantioselective synthesis of the C9-C15 portion (+)-zwittermicin is reported that exploits directional functionalization known hepta-2,5-diyne-1,7-diol by partial reduction two triple bonds followed Sharpless asymmetric epoxidation and boron-directed double ring-opening with sodium azide under Miyashita conditions. Subsequent desymmetrization C(2)-symmetric diazidotetraol product converges upon (-)-3--the enantiomer key intermediate our earlier structural proof (-)-zwittermicin A--and constitutes a formal (+)-zwitttermicin A.
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E V Stabb, L M Jacobson, J Handelsman, Zwittermicin A-producing strains of Bacillus cereus from diverse soils. Applied and Environmental Microbiology. ,vol. 60, pp. 4404- 4412 ,(1994) , 10.1128/AEM.60.12.4404-4412.1994
Peter G. M. Wuts, Theodora W. Greene, Protective groups in organic synthesis ,(1981)
Abderrahim Bouzide, Gilles Sauvé, Highly selective silver(I) oxide mediated monoprotection of symmetrical diols Tetrahedron Letters. ,vol. 38, pp. 5945- 5948 ,(1997) , 10.1016/S0040-4039(97)01328-2
Tsutomu Katsuki, K. Barry Sharpless, First practical method for asymmetric epoxidation Journal of the American Chemical Society. ,vol. 102, pp. 5974- 5976 ,(1981) , 10.1021/JA00538A077
Changming Zhao, Yi Luo, Chunxu Song, Zhongxin Liu, Shouwen Chen, Ziniu Yu, Ming Sun, Identification of three Zwittermicin A biosynthesis-related genes from Bacillus thuringiensis subsp. kurstaki strain YBT-1520 Archives of Microbiology. ,vol. 187, pp. 313- 319 ,(2007) , 10.1007/S00203-006-0196-3
Naoki Yamazaki, Chihiro Kibayashi, Asymmetric synthesis with α,β-bis[(methoxymethyl)oxy] ketones. Enantioselective total synthesis of natural (+)-indolizidine 195B (bicyclic gephyrotoxin 195B) and (-)-pinidine and their enantiomers from a common chiral synthon Journal of the American Chemical Society. ,vol. 111, pp. 1396- 1408 ,(1989) , 10.1021/JA00186A038
Minoru Sasaki, Keiji Tanino, Atsushi Hirai, Masaaki Miyashita, None, The C2 selective nucleophilic substitution reactions of 2,3-epoxy alcohols mediated by trialkyl borates: the first endo-mode epoxide-opening reaction through an intramolecular metal chelate. Organic Letters. ,vol. 5, pp. 1789- 1791 ,(2003) , 10.1021/OL034455F
Eric V. Stabb, Jo Handelsman, Genetic analysis of zwittermicin A resistance in Escherichia coli: effects on membrane potential and RNA polymerase. Molecular Microbiology. ,vol. 27, pp. 311- 322 ,(1998) , 10.1046/J.1365-2958.1998.00678.X
Elizabeth A. Stohl, Jocelyn L. Milner, Jo Handelsman, Zwittermicin A biosynthetic cluster. Gene. ,vol. 237, pp. 403- 411 ,(1999) , 10.1016/S0378-1119(99)00315-7
Hongbin Zhai, Peng Liu, Shengjun Luo, Fang, Mingyue Zhao, A facile synthesis of cis-1-methyl-1,2,3,3a,4,8b- hexahydropyrrolo[3,2-f]pyrindine, an annulated nicotine analog. Organic Letters. ,vol. 4, pp. 4385- 4386 ,(2002) , 10.1021/OL026876N