Application of an ortho-Formylation Reaction in One-pot Procedures and Natural Product Syntheses
Appears in the following Collection
- Farmasøytisk institutt 
AbstractThis thesis describes the transformation of phenols into ortho-hydroxycinnamates, salicylamines, benzoxazines, and salicylnitriles in good overall yields by simple, regioselective, and one-pot procedures using a combination of MgCl2-Et3N as a base system. These one-pot processes are more economically and environmentally benign than those methods previously reported. The MgCl2-Et3N base system was also used in a regioselective Mannich reaction.
Moreover, the first total synthesis of (±)-powelline was described in 10% overall yield over eight steps using an ortho-formylation reaction and an intramolecular oxidative phenolic coupling reaction as the key reactions. The first total synthesis of the naturally occurring all-(Z)-5,7-dihydroxy-2-(4,7,10,13,16-nonadecapentaenyl)chromone was also achieved in six steps from the ethyl ester of eicosapentaenoic acid with an overall of 14% yield.
List of papers
1. Hany F. Anwar , Lars Skattebøl. Jan Skramstad and Trond Vidar Hansen. A one-pot synthesis of ortho-hydroxycinnamate esters. Tetrahedron lett. , 2005, 46, 5285-5287.
2. Hany F. Anwar, Lars Skattebøl and Trond Vidar Hansen. Synthesis substituted salicylamines and dihydro-2H-1,3-benzoxazines. Tetrahedron, 2007, (63), 9997-10002.
3. Hany F. Anwar and Trond Vidar Hansen. A one-pot synthesis of substituted salicylnitriles. Tetrahedron Letters, 2008, 49, 4443-4445.
4. Hany F. Anwar and Trond Vidar Hansen. First total synthesis of (+-)-Powelline. SYNLETT, 2008, 17, 2681-2683.
5. Hany F. Anwarand Trond Vidar Hansen. First total synthesis of a polyunsaturated chromone metabolite isolated from the brown algae Zonaria tournefortii. Organic Letters, 2009,11, 587-588.