Construction of fused bis(pyran) units from enones via a hydrosilylation-dihydroxylation-acetalization-reduction sequence.
HWE coupling of two simple bifunctional fragments provides enones that can be subjected to a four-step sequence to furnish trans-fused bis(pyrans) in good overall yield.
Liu
Xuan
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Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB T6G 2G2, Canada.
West
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D000080:Acetals / Q000138:chemical synthesis / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis / Q000737:chemistry; D005233:Fatty Alcohols / Q000737:chemistry; D006900:Hydroxylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
D000080:Acetals; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004988:Ethers, Cyclic; D005233:Fatty Alcohols; D011714:Pyrans; D012821:Silanes; C512918:triethylsilane; C011159:acyloin