The biomimetic synthesis of SNF4435C and SNF4435D, and the total synthesis of the polyene metabolites aureothin, N-acetyl-aureothamine and spectinabilin

Autor:	Jack E. Baldwin, Robert M. Adlington, John E. Moses, Mikkel F. Jacobsen
Rok vydání:	2006
Předmět:	Spectinabilin Stereochemistry Organic Chemistry Total synthesis Metathesis Polyene Biochemistry Cycloaddition chemistry.chemical_compound Stereospecificity Suzuki reaction chemistry Biomimetic synthesis Drug Discovery
Zdroj:	Tetrahedron. 62:1675-1689
ISSN:	0040-4020
DOI:	10.1016/j.tet.2005.11.058
Popis:	Full details of the biomimetic conversion of polyene metabolite spectinabilin (5) into the isomeric natural products SNF4435C (1) and SNF4435D (2) by a cascade of E/Z-isomerizations and electrocyclizations are reported. Additionally, short total syntheses of the related natural products (±)-aureothin (3), (±)-N-acetyl-aureothamine (4) and (±)-spectinabilin (5) are presented. The key steps in the synthesis of (±)-3, (±)-4 and (±)-5 are the construction of the tetrahydrofuran motif using a palladium-catalyzed cycloaddition and the ruthenium-catalyzed cross metathesis of alkene 17 to form the common intermediate, boronic ester 24, which was further transformed using a trans-selective Suzuki coupling with a dibromide and a stereospecific Negishi-type methylation.
Databáze:	OpenAIRE
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