title: Search for highly efficient, stereoselective, and practical synthesis of complex organic compounds of medicinal importance as exemplified by the synthesis of the C21-C37 fragment of amphotericin B.
abstract: Highly stereoselective: A highly efficient, stereoselective and practical synthesis of the C21-C37 fragment of amphotericin B was realized in 25 % overall yield in eight longest linear steps from commercially available ethyl (S)-3-hydroxybutyrate by using Fráter-Seebach alkylation, Brown crotylboration, Negishi coupling, Heck reaction, and Horner-Wadsworth-Emmons (HWE) olefination as key steps (see diagram).
authors.affiliation: Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907-2084 (USA).
authors.forename: Guangwei
authors.initials: G
authors.lastname: Wang
authors.forename: Shiqing
authors.initials: S
authors.lastname: Xu
authors.forename: Qian
authors.initials: Q
authors.lastname: Hu
authors.forename: Fanxing
authors.initials: F
authors.lastname: Zeng
authors.forename: Ei-ichi
authors.initials: E
authors.lastname: Negishi
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000478:Alkylation; D000666:Amphotericin B / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000666:Amphotericin B
keywords: Negishi coupling; amphotericin B; cross-coupling; natural products; synthesis
references.citation: Isr J Chem. 2010 Dec 1;50(5-6):696-701
references.pmid: 23966749
references.citation: J Org Chem. 2000 Nov 17;65(23):7959-70
references.pmid: 11073604
references.citation: Angew Chem Int Ed Engl. 2000 Dec 1;39(23):4364-4366
references.pmid: 29711926
references.citation: Org Lett. 2006 Aug 17;8(17):3675-8
references.pmid: 16898789
references.citation: Angew Chem Int Ed Engl. 2007;46(16):2768-813
references.pmid: 17410611
references.citation: Org Lett. 2004 Aug 19;6(17):2913-6
references.pmid: 15330646
references.citation: Angew Chem Int Ed Engl. 2011 Jul 18;50(30):6738-64
references.pmid: 21717531
references.citation: Bioorg Med Chem. 2009 Mar 15;17(6):2290-303
references.pmid: 19028103
references.citation: Chem Rev. 2007 Mar;107(3):874-922
references.pmid: 17305399
references.citation: Antibiot Annu. 1955-1956;3:587-91
references.pmid: 13355331
references.citation: J Am Chem Soc. 1986 Sep 1;108(19):5919-23
references.pmid: 22175350
references.citation: Adv Synth Catal. 2011 Nov;353(16):2981-2987
references.pmid: 24072993
references.citation: J Org Chem. 2010 May 21;75(10):3151-82
references.pmid: 20465291
references.citation: J Am Chem Soc. 2008 Jan 16;130(2):466-8
references.pmid: 18081295
references.citation: J Am Chem Soc. 1971 Sep 8;93(18):4560-4
references.pmid: 5131155
references.citation: Proc Natl Acad Sci U S A. 2011 Jul 12;108(28):11344-9
references.pmid: 21709262