ChemInform Abstract: Natural Products Synthesis by retro-Diels—Alder Reactions. Part 15. Using a Rigid Molecule Tricyclodecadienone for the Stereospecific Synthesis of the Chain Compound Senecivernic Acid.
✍ Scribed by Z.-Y. LIU; L.-Y. ZHAO; Y.-N. XIE; Y. WU; L.-L. WONG; H. ZHENG
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 39 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Natural Products Synthesis by retro-Diels-Alder Reactions. Part 15. Using a Rigid Molecule Tricyclodecadienone for the Stereospecific Synthesis of the Chain Compound Senecivernic Acid.
-A highly efficient synthesis of senecivernic acid (XV), a metabolite of the pyrrolizidine alkaloid senecivernine, is presented involving the stereoselective introduction of the methyl groups into compounds (I), (V) and (VIII), the thermal retro Diels-Alder reaction of tricyclodecenone (VII) and Baeyer-Villiger oxidation of the cyclopentanone (IX) as the key steps. The synthesis is achieved in ten steps in 50 % overall yield without the use of protecting groups. -(LIU, Z.-Y.;