3-Hydroxyleukotriene B4 (3-OH-LTB4): Total Synthesis and Stereochemical Assignment.

RK Bhatt, K Chauhan, P Wheelan…

Index: Bhatt, Rama K.; Chauhan, Kamlesh; Wheelan, Pat; Murphy, Robert C.; Falck Journal of the American Chemical Society, 1994 , vol. 116, # 12 p. 5050 - 5056

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Citation Number: 31

Abstract

Abstract: The asymmetric total synthesis of 3-hydroxyleukotriene B4 (3-OH-LTB4), an ethanol-inducible proinflammatory autacoid, was achieved using a triply convergent strategy for the sequential union of propargylic arsonium salt 3 with pyranosides 24b and furanose 4. Both saccharide subunits were derived from commercial 2-deoxy-~-ribose. The key transformation involved palladium-mediated coupling of bromoacetylenide 9 with ...