title: Enantioselective synthesis of (+)-crocacin C. An example of a highly challenging mismatched double asymmetric δ-stannylcrotylboration reaction.
abstract: A concise, enantioselective synthesis of (+)-crocacin C is described, featuring a highly diastereoselective mismatched double asymmetric δ-stannylcrotylboration of the stereochemically demanding chiral aldehyde 9 with the bifunctional crotylborane reagent (S)-E-10. The total synthesis of (+)-crocacin C was accomplished in seven steps (longest linear sequence) starting from commercially available precursors.
authors.affiliation: Department of Chemistry, Scripps Florida, Jupiter, Florida 33458, USA.
authors.forename: Ming
authors.initials: M
authors.lastname: Chen
authors.forename: William R
authors.initials: WR
authors.lastname: Roush
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009231:Myxococcales / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014001:Tin / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000475:Alkenes; D000577:Amides; D009942:Organometallic Compounds; C500918:crocacin C; D014001:Tin