Studies on tumor promoters. 10. Synthesis of the abc ring system of the tiglianes and daphnanes by a zirconium-mediated intramolecular enyne carbocyclization
✍ Scribed by Paul A. Wender; Frank E. McDonald
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 295 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
A novel synthetic route to the ABC ring system of the daphnanes and tiglianes based on intramolecular enyne carbocyclixation is described that provides access to a new family of diterpene tumor promoter analogs. Phorbol lZmyristate 13-acetate has long been of interest in cancer research as one of the most potent tumor promoters in multistage carcinogenesis. 2 More recently, phorbol esters and strccturally analogous daphnanes and ingenanes (Scheme 1) have also been found to exhibit a wide atray of other biological activities, providing new leads for chemotherapeutic design. The regulatory enzyme protein kinase C (PKC) has been identified as the primary receptor for many of these compounds? SCHEME 1 phorbol 12-myristate 13-acetate (tigliaoe) gnidimacrin (daphnane) ingenol 3-tetradecanoete Cigemme)