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Development of an Oxazole Conjunctive Reagent and Application to the Total Synthesis of Siphonazoles

TitleDevelopment of an Oxazole Conjunctive Reagent and Application to the Total Synthesis of Siphonazoles
Publication TypeJournal Article
Year of Publication2009
AuthorsZhang, JM, Polishchuk, EA, Chen, J, Ciufolini, MA
JournalJournal of Organic Chemistry
Volume74
Pagination9140-9151
Date PublishedDec
Type of ArticleReview
ISBN Number0022-3263
Keywords1ST TOTAL-SYNTHESIS, ALLENYL ESTERS, CONJUGATED, CYANOBACTERIUM NOSTOC-MUSCORUM, CYTOTOXIC, DIAZONAMIDE-A, DOUBLE ELIMINATION PROTOCOL, GLYOXYLIC-ACID DERIVATIVES, INTRAMOLECULAR HYDROAMINATION, marine sponge, METABOLITES, NATURAL-PRODUCT HENNOXAZOLE
Abstract

The preparation of 4-carbethoxy-5-methyl-2-(phenylsulfonyl)methyloxizole and Its use in the elaboration of more complex oxazoles are described. A total synthesis of the unique natural products siphonazoles A and B, illustrates an application of this building block. A discussion of the biological activity of the siphonazoles is also presented.
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