title: Substrate and stereocontrolled iodocycloetherification of highly functionalized enantiomerically pure allylic alcohols: application to synthesis of cytotoxic 2-epi jaspine B and its biological evaluation.
abstract: Stereoselectivities of electrophilic additions of molecular iodine to enantiomerically pure highly functionalized allylic alcohols with internal nucleophiles have been investigated. The intramolecular nucleophilic attack on the I2-π complex by an oxygen nucleophile to obtain tri- and tetrasubstituted THFs is highly regio-, stereoselective and substrate controlled. The application of this study has been shown by utilizing one of the THFs 4a as a key intermediate to complete the total synthesis of marine anti-cancer natural product 2-epi jaspine B.
authors.affiliation: Division of Medicinal and Process Chemistry, CSIR-Central Drug Research Institute, Lucknow, 226 031, India. akshaw55@yahoo.com.
authors.forename: Somireddy
authors.initials: S
authors.lastname: Kundooru
authors.forename: Pintu
authors.initials: P
authors.lastname: Das
authors.forename: Sanjeev
authors.initials: S
authors.lastname: Meena
authors.forename: Vikash
authors.initials: V
authors.lastname: Kumar
authors.forename: Mohammad Imran
authors.initials: MI
authors.lastname: Siddiqi
authors.forename: Dipak
authors.initials: D
authors.lastname: Datta
authors.forename: Arun K
authors.initials: AK
authors.lastname: Shaw
mesh_terms: D016923:Cell Death / Q000187:drug effects; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003500:Cyclization; D004987:Ethers / Q000737:chemistry*; D006801:Humans; D020128:Inhibitory Concentration 50; D007454:Iodides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D020005:Propanols / Q000737:chemistry*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology / Q000633:toxicity; D013237:Stereoisomerism
chemical_list: D004987:Ethers; D007454:Iodides; D020005:Propanols; C468594:pachastrissamine; C006463:allyl alcohol; D013110:Sphingosine