Jacobsen, Mikkel F., Moses, John E., Adlington, Robert M., Baldwin, Jack E. (2006) The biomimetic synthesis of SNF4435C and SNF4435D, and the total synthesis of the polyene metabolites aureothin, N-acetyl-aureothamine and spectinabilin. Tetrahedron, 62 (8). pp. 1675-1689. ISSN 0040-4020
Abstract
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.
| Item Type: | Paper |
|---|---|
| Uncontrolled Keywords: | Metabolite Total synthesis Metathesis C–C coupling reaction Biomimetic synthesis Electrocyclization Isomerization |
| CSHL Authors: | |
| Depositing User: | Matthew Dunn |
| Date: | 2006 |
| Date Deposited: | 17 Nov 2020 21:32 |
| Last Modified: | 17 Nov 2020 21:32 |
| URI: | https://repository.cshl.edu/id/eprint/39793 |
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