An investigation into the total synthesis of clerocidin: stereoselective synthesis of a clerodane intermediate
A key clerodane intermediate was prepared during the investigation of the total synthesis of clerocidin. The diterpene backbone was synthesized by an enantioselective Robinson annulation followed by trapping of the enolate using allyl bromide. Selective hydrogenation conditions were developed to int...
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| Published in: | Tetrahedron: asymmetry Vol. 9; no. 18; pp. 3179 - 3183 |
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| Main Authors: | , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
Elsevier Ltd
18-09-1998
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| Online Access: | Get full text |
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| Summary: | A key clerodane intermediate was prepared during the investigation of the total synthesis of clerocidin. The diterpene backbone was synthesized by an enantioselective Robinson annulation followed by trapping of the enolate using allyl bromide. Selective hydrogenation conditions were developed to introduce the axial methyl group at the C
8 position. A palladium-mediated carbonylation reaction was employed to generate the key α,β-unsaturated dialdehyde. |
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| ISSN: | 0957-4166 1362-511X |
| DOI: | 10.1016/S0957-4166(98)00349-8 |