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Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-lodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal DeCanolides and Derivatives

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dc.contributor.authorSherwood, Alexander M.
dc.contributor.authorWilliamson, Samuel E.
dc.contributor.authorJohnson, Stephanie N.
dc.contributor.authorYilmaz, ANIL
dc.contributor.authorDay, Victor W.
dc.contributor.authorPrisinzano, Thomas E.
dc.contributor.institutionauthorYILMAZ, ANIL
dc.date.accessioned2019-10-05T13:39:14Z
dc.date.available2019-10-05T13:39:14Z
dc.date.issued2018-01-19
dc.description.abstractA reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated by providing access to known fungal decanolides as well as novel aromatic macrocycles. The protocol provided a gram-scale route to (-)-aspinolide A and (-)-5-epi-aspinolide A utilizing a catalytic Nozaki-Hiyama-Kishi reaction to close the macrolide in the final step in 65-84% yields.
dc.identifier
dc.identifier.citationSherwood A. M. , Williamson S. E. , Johnson S. N. , Yilmaz A., Day V. W. , Prisinzano T. E. , -Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-lodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal DeCanolides and Derivatives-, JOURNAL OF ORGANIC CHEMISTRY, cilt.83, ss.980-992, 2018
dc.identifier.urihttps://hdl.handle.net/20.500.12645/2635
dc.language.isoen
dc.rightsinfo:eu-repo/semantics/openAccess
dc.titleScalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-lodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal DeCanolides and Derivatives
dc.typeArticle
dspace.entity.typePublication
local.article.journalnameKlinik Gelişim
local.avesis.id4084241e-9bdb-4c35-be79-2e7f7cb0b859
local.avesis.response2505
relation.isAuthorOfPublication9c5ef152-9387-4153-86b3-556fc729d785
relation.isAuthorOfPublication.latestForDiscovery9c5ef152-9387-4153-86b3-556fc729d785
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