Cross dehydrogenative coupling of sugar enol ethers with terminal alkenes in the synthesis of pseudo-disaccharides, chiral oxadecalins and a conjugated triene

文献情報

出版日 2018-03-15

DOI 10.1039/C8OB00168E

インパクトファクター 3.876

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要旨

An efficient strategy for the synthesis of C-2 and C-3 branched sugar dienes via cross dehydrogenative coupling of sugar enol ethers with terminal alkenes was developed. Both pyran and furan based enol ethers coupled smoothly with electron rich as well as deficient alkene sources yielding sugar dienes with complete E-stereoselectivity. This coupling reaction was applied successfully for the synthesis of orthogonally protected pseudo-C-saccharides as an alternative to olefin metathesis. Substrate scope was further enhanced by reacting exoglycals with methyl acrylate to generate C-5 branched sugars with moderate diastereoselectivity. These diene subunits were reacted with maleic anhydride under [4 + 2] cycloaddition conditions to generate highly functionalised chiral oxadecalin cores. Finally, utilizing this C–C bond formation, a sugar based conjugated triene was synthesized in excellent yield and selectivity.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Cross dehydrogenative coupling of sugar enol ethers with terminal alkenes in the synthesis of pseudo-disaccharides, chiral oxadecalins and a conjugated triene

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Organic & Biomolecular Chemistry

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