Filling some blanks in a divergent approach to gabosines : enantioselective synthesis of (-)-epiepoxydon, (+)-phyllostine, (-)-gabosine D, and (-)-gabosine E
Fresneda, Miguel Ángel (Universitat Autònoma de Barcelona. Departament de Química)
Alibes, Ramón (Universitat Autònoma de Barcelona. Departament de Química)
Bayón, Joan Carles (Universitat Autònoma de Barcelona. Departament de Química)
Figueredo Galimany, Marta (Universitat Autònoma de Barcelona. Departament de Química)

Date:	2016
Abstract:	The levorotatory enantiomers of gabosines D and E were synthesized through a divergent approach that could equally well be applied to the synthesis of the dextrorotatory enantiomers, which have been isolated from natural sources. The approach relies on an initial desymmetrization of p-methoxyphenol, followed by an enzymatic resolution that separately provides the two enantiomers of synthon 3. This versatile synthon can be further transformed into the diverse polyoxygenated cyclohexane target molecules. Key steps in the synthesis of (-)-gabosines D and E from (4R,6S)-3 are the stereoselective hydroxymethylation at the α-carbonyl position leading to (+)-4, and the subsequent reagent-controlled epoxidation of the carbon-carbon double bond. A branching in the sequence also allowed the synthesis of the anhydrogabosines (-)-epiepoxydon and (+)-phyllostine.
Rights:	Tots els drets reservats.
Language:	Anglès
Document:	Article ; recerca ; Versió acceptada per publicar
Subject:	Cyclitols ; Divergent synthesis ; Eantioselectivity ; Gabosines ; Natural products
Published in:	European journal of organic chemistry, Vol. 2016, issue 21 (July 2016) , p. 3568-3574, ISSN 1099-0690

DOI: 10.1002/ejoc.201600492

Postprint 9 p, 861.1 KB

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Research literature > UAB research groups literature > Research Centres and Groups (research output) > Experimental sciences > Synthesis of Bioactive Organic Compounds and Functional Materials (SynOrgFUN)
Articles > Research articles
Articles > Published articles