A Novel Synthesis of Conduritol-C and Conduritol-E via p-Benzoquinone
A new and stereospecific synthesis for Conduritol-C 8 and Conduritol-E 13a has been developed starting from p-benzoquinone 1. 1,4-oxygen functionalities were introduced in both synthesis by the reduction of dibromo p-benzoquinone 2 with NaBH 4 . 2,3-oxygen functionalities were introduced by KMnO 4 o...
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| Veröffentlicht in: | Synthetic communications 1992-09, Vol.22 (18), p.2613-2619 |
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| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | A new and stereospecific synthesis for Conduritol-C 8 and Conduritol-E 13a has been developed starting from p-benzoquinone 1. 1,4-oxygen functionalities were introduced in both synthesis by the reduction of dibromo p-benzoquinone 2 with NaBH
4
. 2,3-oxygen functionalities were introduced by KMnO
4
oxidation of 4 for Conduritol C 8. Oxidation of 3 with m-chloroperbenzoic acid gave 9. Acid-catalyzed ring opening reaction of 9 gave 10a which leads to Conduritol-E. |
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| ISSN: | 0039-7911 1532-2432 |
| DOI: | 10.1080/00397919208021660 |