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dc.contributor.authorPowers, Zacharyen_US
dc.contributor.authorScharf, Adamen_US
dc.contributor.authorCheng, Andreaen_US
dc.contributor.authorYang, Fengen_US
dc.contributor.authorHimmelbauer, Martinen_US
dc.contributor.authorMitsuhashi, Takaakien_US
dc.contributor.authorBarra, Lenaen_US
dc.contributor.authorTaniguchi, Yoshimasaen_US
dc.contributor.authorKikuchi, Takashien_US
dc.contributor.authorFujita, Makotoen_US
dc.contributor.authorAbe, Ikuroen_US
dc.contributor.authorPorco, John A.en_US
dc.coverage.spatialGermanyen_US
dc.date.accessioned2020-12-15T15:57:01Z
dc.date.available2020-12-15T15:57:01Z
dc.date.issued2019-11-04
dc.identifierhttps://www.ncbi.nlm.nih.gov/pubmed/31515901
dc.identifier.citationZachary Powers, Adam Scharf, Andrea Cheng, Feng Yang, Martin Himmelbauer, Takaaki Mitsuhashi, Lena Barra, Yoshimasa Taniguchi, Takashi Kikuchi, Makoto Fujita, Ikuro Abe, John A Porco. 2019. "Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization.." Angew Chem Int Ed Engl, Volume 58, Issue 45, pp. 16141 - 16146. https://doi.org/10.1002/anie.201910710
dc.identifier.issn1521-3773
dc.identifier.urihttps://hdl.handle.net/2144/41804
dc.descriptionPublished in final edited form as: Angew Chem Int Ed Engl. 2019 November 04; 58(45): 16141–16146. doi:10.1002/anie.201910710.en_US
dc.description.abstractA biomimetic route to farnesyl pyrophosphate and dimethyl orsellinic acid (DMOA)-derived meroterpenoid scaffolds has yet to be reported despite great interest from the chemistry and biomedical research communities. A concise synthetic route with the potential to access DMOA-derived meroterpenoids is highly desirable to create a library of related compounds. Herein, we report novel dearomatization methodology followed by polyene cyclization to access DMOA-derived meroterpenoid frameworks in six steps from commercially available starting materials. Furthermore, several farnesyl alkene substrates were used to generate structurally novel, DMOA-derived meroterpenoid derivatives. DFT calculations combined with experimentation provided a rationale for the observed thermodynamic distribution of polycyclization products.en_US
dc.description.sponsorshipP50 GM067041 - NIGMS NIH HHS; R35 GM118173 - NIGMS NIH HHS; GM-118173 - NIGMS NIH HHS; JP16H06443 - Japan Society for the Promotion of Scienceen_US
dc.format.extentp. 16141 - 16146en_US
dc.languageeng
dc.language.isoen_US
dc.relation.ispartofAngew Chem Int Ed Engl
dc.subject3,5-dimethylorsellinic aciden_US
dc.subjectBiosynthesisen_US
dc.subjectDearomatizationen_US
dc.subjectMeroterpenoidsen_US
dc.subjectPolyene cyclizationen_US
dc.subjectBiomimeticsen_US
dc.subjectCyclizationen_US
dc.subjectPolyenesen_US
dc.subjectPolyisoprenyl phosphatesen_US
dc.subjectSesquiterpenesen_US
dc.subjectTerpenesen_US
dc.subjectOrganic chemistryen_US
dc.subjectChemical sciencesen_US
dc.titleBiomimetic synthesis of meroterpenoids by dearomatization-driven polycyclizationen_US
dc.typeArticleen_US
dc.description.versionAccepted manuscripten_US
dc.identifier.doi10.1002/anie.201910710
pubs.elements-sourcepubmeden_US
pubs.notesEmbargo: Not knownen_US
pubs.organisational-groupBoston Universityen_US
pubs.organisational-groupBoston University, College of Arts & Sciencesen_US
pubs.organisational-groupBoston University, College of Arts & Sciences, Department of Chemistryen_US
pubs.publication-statusPublisheden_US
dc.identifier.mycv488547


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