An IMDA Approach to Tigliane and Daphnane Diterpenoids: Generation of the Tetracyclic Ring System of the Tiglianes. -The tetracyclic compound (V) representing the ring system of phorbol and other tigliane diterpenes is prepared using an unusual intramolecular Diels-Alder reaction of (I) followed by
An IMDA approach to tigliane and daphnane diterpenoids: Generation of the tetracyclic ring system of the tiglianes
โ Scribed by Philip C Bulman Page; David C Jennens; Heather McFarland
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 253 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
A synthesis of the tetracyclic ring system of phorbol and other tigliane diterpenes has been achieved in six steps using an unusual intrarnolecular Diels-Alder reaction both as the key stereocontrolling process and to introduce a double bond appropriately positioned for functionalization as a cyclopropane.
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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 th