A Chemoenzymatic Total Synthesis of the Protoilludane Aryl Ester (+)-Armillarivin
The title natural product, 1, has been synthesized in 20 steps from the enantiomerically pure cis-1,2-dihydrocatechol 2, itself obtained through the whole-cell biotransformation of toluene. The pivotal steps in the reaction sequence involve a Diels–Alder cycloaddition reaction between diene 2 and cy...
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| Veröffentlicht in: | Organic letters 2013-04, Vol.15 (8), p.1934-1937 |
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| Hauptverfasser: | , , , , |
| Format: | Artikel |
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| container_end_page | 1937 |
|---|---|
| container_issue | 8 |
| container_start_page | 1934 |
| container_title | Organic letters |
| container_volume | 15 |
| creator | Schwartz, Brett D Matoušová, Eliška White, Richard Banwell, Martin G Willis, Anthony C |
| description | The title natural product, 1, has been synthesized in 20 steps from the enantiomerically pure cis-1,2-dihydrocatechol 2, itself obtained through the whole-cell biotransformation of toluene. The pivotal steps in the reaction sequence involve a Diels–Alder cycloaddition reaction between diene 2 and cyclopentenone (3) and the photochemically promoted 1,3-acyl rearrangement of the bicyclo[2.2.2]oct-4-en-1-one 20 derived from the cycloadduct 4. |
| doi_str_mv | 10.1021/ol400583c |
| format | Article |
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| ispartof | Organic letters, 2013-04, Vol.15 (8), p.1934-1937 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Biological Products - chemical synthesis Biological Products - chemistry Cyclopentanes - chemistry Esters Molecular Structure Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Stereoisomerism |
| title | A Chemoenzymatic Total Synthesis of the Protoilludane Aryl Ester (+)-Armillarivin |
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