Author, as appears in the article.: Carreras, Javier; Livendahl, Madeleine; McGonigal, Paul R; Echavarren, Antonio M
Department: Química Analítica i Química Orgànica
URV's Author/s: ECHAVARREN PABLOS, ANTONIO
Keywords: Total synthesis Total synthesi Terpenoids Sesquiterpenoids Rearrangement reactions Natural products Gold Essential oils Diterpenoids Cyclization Chemistr Catalyzed cycloisomerization Aromadendrane derivatives (+)-aromadendrene terpenoids natural products gold cyclization
Abstract: Three natural aromadendrane sesquiterpenes, (-)-epiglobulol, (-)-4,7-aromadendranediol, and (-)-4,7-aromadendranediol, have been synthesized in only seven steps in 12, 15, and 17% overall yields, respectively, from (E,E)-farnesol by a stereodivergent gold(I)-catalyzed cascade reaction which forms the tricyclic aromadendrane core in a single step. These are the shortest total syntheses of these natural compounds.
Thematic Areas: Química Medicina ii Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Astronomia / física
licence for use: https://creativecommons.org/licenses/by/3.0/es/
Author's mail: antoniomaria.echavarren@urv.cat
Author identifier: 0000-0002-6418-7930
Record's date: 2025-02-18
Paper version: info:eu-repo/semantics/publishedVersion
Paper original source: Angewandte Chemie (International Ed. Print). 53 (19): 4896-4899
APA: Carreras, Javier; Livendahl, Madeleine; McGonigal, Paul R; Echavarren, Antonio M (2014). Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (-)-Epiglobulol and (-)-4β,7α- and (-)-4α,7α-Aromadendranediols. Angewandte Chemie (International Ed. Print), 53(19), 4896-4899. DOI: 10.1002/anie.201402044
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Entity: Universitat Rovira i Virgili
Journal publication year: 2014
Publication Type: Journal Publications