title: Asymmetric Total Synthesis of (-)-Erogorgiaene and Its C-11 Epimer and Investigation of Their Antimycobacterial Activity.
abstract: A short, nine-step, highly enantioselective synthesis of (-)-erogorgiaene and its C-11 epimer is reported. The key stereochemistry controlling steps involve catalytic asymmetric crotylation, anionic oxy-Cope rearrangement and cationic cyclisation. (-)-Erogorgiaene exhibited promising antitubercular activity against multidrug-resistant strains of Mycobacterium tuberculosis.
authors.affiliation: Department of Chemistry, Loughborough University, Loughborough, LE11 3TU, UK.
authors.forename: Celia A
authors.initials: CA
authors.lastname: Incerti-Pradillos
authors.affiliation: Department of Chemistry, Loughborough University, Loughborough, LE11 3TU, UK.
authors.forename: Mikhail A
authors.initials: MA
authors.lastname: Kabeshov
authors.affiliation: Department of Chemistry, Loughborough University, Loughborough, LE11 3TU, UK.
authors.forename: Paul S
authors.initials: PS
authors.lastname: O'Hora
authors.affiliation: Department of Chemistry, Loughborough University, Loughborough, LE11 3TU, UK.|Department of Chemistry, Perm State University, Bukireva 15, 614990, Perm, Russia.
authors.forename: Sergei A
authors.initials: SA
authors.lastname: Shipilovskikh
authors.affiliation: Department of Chemistry, Perm State University, Bukireva 15, 614990, Perm, Russia.
authors.forename: Aleksandr E
authors.identifier: http://orcid.org/0000-0002-4299-3464
authors.initials: AE
authors.lastname: Rubtsov
authors.affiliation: Department of Chemistry, Perm State University, Bukireva 15, 614990, Perm, Russia.
authors.forename: Vera A
authors.initials: VA
authors.lastname: Drobkova
authors.affiliation: Department of Chemistry, Perm State University, Bukireva 15, 614990, Perm, Russia.
authors.forename: Svetlana Yu
authors.initials: SY
authors.lastname: Balandina
authors.affiliation: Department of Chemistry, Loughborough University, Loughborough, LE11 3TU, UK. A.Malkov@lboro.ac.uk.|Chemistry Department, Peoples' Friendship University of Russia, Miklukho-Maklaya 6, 117198, Moscow, Russia. A.Malkov@lboro.ac.uk.
authors.forename: Andrei V
authors.identifier: http://orcid.org/0000-0001-6072-2353
authors.initials: AV
authors.lastname: Malkov
mesh_terms: D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D060326:Chemistry Techniques, Synthetic / Q000379:methods; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D013237:Stereoisomerism; D014376:Tuberculosis / Q000188:drug therapy
chemical_list: D000995:Antitubercular Agents; D004224:Diterpenes; C428183:erogorgiaene
keywords: allylation; asymmetric catalysis; enantioselectivity; rearrangement; total synthesis