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pubmed-article:15049631pubmed:abstractTextA modular synthesis of the lamellarin family of natural products has been developed that is based on the application of three iterative halogenation/cross-coupling reaction sequences. The ability to halogenate the pyrrole core in a regioselective fashion, even in the presence of highly electron-rich aryl substituents, has been established. The compatibility of Suzuki coupling conditions with free alcohols and phenols in the boronic acids has been employed to reduce the number of protection/deprotection steps. Indeed, the presence of a free phenol on boronic acid 3 has been determined to be critical for the successful final coupling in route to lamellarin G trimethyl ether, since protected versions fail to undergo coupling.lld:pubmed
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pubmed-article:15049631pubmed:dateRevised2006-11-15lld:pubmed
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pubmed-article:15049631pubmed:articleTitleA modular synthesis of the lamellarins: total synthesis of lamellarin G trimethyl ether.lld:pubmed
pubmed-article:15049631pubmed:affiliationDepartment of Chemistry, State University of New York at Binghamton, Binghamton, New York 13902, USA. shandy@binghamton.edulld:pubmed
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pubmed-article:15049631pubmed:publicationTypeResearch Support, Non-U.S. Gov'tlld:pubmed
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