Total synthesis of (-)-hapalindole G: A novel tin-mediated indole synthesis

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dc.contributor.advisorFukuyama, Tohru
dc.creatorChen, Xiaoqi
dc.date.accessioned2009-06-04T00:11:33Z
dc.date.available2009-06-04T00:11:33Z
dc.date.issued1994
dc.description.abstractThe first total synthesis of ($-$)-hapalindole G, a member of novel chlorine- and isonitrile-containing hapalindoles from the cultured cyanophyte Hapalosiphon fontinalis, is accomplished. Our 21-step synthesis of ($-$)-hapalindole G from ($-$)-carveol features a stereospecific introduction of chlorine next to a quaternary center via cleavage of the cyclopropane intermediate and facile elaboration of the indole moiety through a conjugate addition of lithium methyl methylthiomethyl sulfoxide to an enone followed by hydrolysis of the resultant adduct. The absolute configuration of ($-$)-hapalindole G has therefore been confirmed on the basis of the specific rotation of our synthetic sample. Also described herein is a novel tin-mediated radical indole synthesis by using o-isocyanostyrene derivatives as starting materials via 2-tri-n-butylstannyl-3-substituted indoles as intermediates. The 2-tri-n-butylstannyl-indoles were also subjected to the one-pot Stille coupling reaction and iodination. The iodoindoles were capable of further manipulation. Our efficient synthesis paves the way for a facile construction of a variety of 3- or 2,3-substituted indoles from readily accessible isonitriles.
dc.format.extent257 p.en_US
dc.format.mimetypeapplication/pdf
dc.identifier.callnoTHESIS CHEM. 1994 CHEN
dc.identifier.citationChen, Xiaoqi. "Total synthesis of (-)-hapalindole G: A novel tin-mediated indole synthesis." (1994) Diss., Rice University. <a href="https://hdl.handle.net/1911/16719">https://hdl.handle.net/1911/16719</a>.
dc.identifier.urihttps://hdl.handle.net/1911/16719
dc.language.isoeng
dc.rightsCopyright is held by the author, unless otherwise indicated. Permission to reuse, publish, or reproduce the work beyond the bounds of fair use or other exemptions to copyright law must be obtained from the copyright holder.
dc.subjectOrganic chemistry
dc.subjectPharmaceutical chemistry
dc.titleTotal synthesis of (-)-hapalindole G: A novel tin-mediated indole synthesis
dc.typeThesis
dc.type.materialText
thesis.degree.departmentChemistry
thesis.degree.disciplineNatural Sciences
thesis.degree.grantorRice University
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy
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