title: Total Synthesis of Peniphenones A-D via Biomimetic Reactions of a Common o-Quinone Methide Intermediate.
abstract: The total synthesis of peniphenones A-D has been achieved via Michael reactions between appropriate nucleophiles and a common o-quinone methide intermediate. This strategy, which was based on a biosynthetic hypothesis, minimized the use of protecting groups and thus facilitated concise syntheses of the natural products. The most complex target, the benzannulated spiroketal peniphenone A, was synthesized enantioselectively in nine linear steps from commercially available starting materials.
authors.affiliation: Department of Chemistry, University of Adelaide , Adelaide, SA 5005, Australia.
authors.forename: Justin T J
authors.initials: JT
authors.lastname: Spence
authors.affiliation: Department of Chemistry, University of Adelaide , Adelaide, SA 5005, Australia.
authors.forename: Jonathan H
authors.initials: JH
authors.lastname: George
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045563:Indolequinones / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D010407:Penicillium / Q000737:chemistry*; D043982:Rhizophoraceae / Q000382:microbiology; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D016227:Benzoquinones; D001688:Biological Products; D045563:Indolequinones; C000606780:peniphenone B; C000606781:peniphenone C; C068040:quinone methide