title: Total Synthesis of (-)-Luminacin D.
abstract: A second-generation synthesis of (-)-luminacin D based on an early stage introduction of the trisubstituted epoxide group is reported, allowing access to the natural product in an improved yield and a reduced number of steps (5.4%, 17 steps vs 2.6%, 19 steps). A full account of the optimization work is provided, with the reversal of stereoselection in the formation of the C4 alcohol in equally excellent diastereoselectivity as the key improvement.
authors.affiliation: Chemistry, University of Southampton , Highfield, Southampton SO17 1BJ, U.K.
authors.forename: Julien
authors.initials: J
authors.lastname: Malassis
authors.affiliation: Chemistry, University of Southampton , Highfield, Southampton SO17 1BJ, U.K.
authors.forename: Nathan
authors.initials: N
authors.lastname: Bartlett
authors.affiliation: Chemistry, University of Southampton , Highfield, Southampton SO17 1BJ, U.K.
authors.forename: Kane
authors.initials: K
authors.lastname: Hands
authors.affiliation: UCB , 216 Bath Road, Slough, Berkshire SL1 WE, U.K.
authors.forename: Matthew D
authors.initials: MD
authors.lastname: Selby
authors.affiliation: Chemistry, University of Southampton , Highfield, Southampton SO17 1BJ, U.K.
authors.forename: Bruno
authors.initials: B
authors.lastname: Linclau
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D001547:Benzaldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D001547:Benzaldehydes; D004852:Epoxy Compounds; D013141:Spiro Compounds; C413565:luminacin D