Synthesis of elemane bis-lactones structurally related to vernolepin
✍ Scribed by Gonzalo Blay; Luz Cardona; Begoña García; Luisa Lahoz; JoséR Pedro
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 191 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The chemical transformation of santonin into an elemane bis-lactone structurally related to the antitumour compound vemolepin is reported. The transformation of ring A of santonin into a hemiacetal ~-lactone was achieved in eleven steps. The spectroscopic characteristics of the synthetic product obtained in this way revealed that the proposed structure for the natural product should be revised.
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Sequences of nine and four steps were designed to yield two tirobifan related macrocycles by SN2 macrocyclization. The cyclic compounds contain the amino acid tyrosine, one insaturation and are either 18-or 20-membered rings. All the reaction conditions are very mild and the overall yields indicate