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  • Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Landry, M. L., Hu, D. X., McKenna, G. M., Burns, N. Z. 2016; 138 (15): 5150-5158

    Abstract

    A titanium-based catalytic enantioselective dichlorination of simple allylic alcohols is described. This dichlorination reaction provides stereoselective access to all common dichloroalcohol building blocks used in syntheses of chlorosulfolipid natural products. An enantioselective synthesis of ent-(-)-deschloromytilipin A and a concise, eight-step synthesis of ent-(-)-danicalipin A are executed and employ the dichlorination reaction as the first step. Extension of this system to enantioselective dibromination and its use in the synthesis of pentabromide stereoarrays relevant to bromosulfolipids is reported. The described dichlorination and dibromination reactions are capable of exerting diastereocontrol in complex settings allowing X-ray crystal structure analysis of natural and unnatural diastereomers of polyhalogenated stereohexads.

    View details for DOI 10.1021/jacs.6b01643

    View details for Web of Science ID 000374812100024

    View details for PubMedID 27018981

    View details for PubMedCentralID PMC4922634