This proposal outlines a strategy for the enantioselective synthesis of (-)- scarbronine A, a complex diterpenoid natural product. The scabronine compounds are potent stimulators of nerve growth factor-synthesis, making them potential therapeutic agents for a variety of nervous system disorders. The proposed strategy utilizes a novel coupling annulation to assemble the seven-membered ring.
Mandal, Mihirbaran; Yun, Heedong; Dudley, Gregory B et al. (2005) Total synthesis of guanacastepene a: a route to enantiomeric control. J Org Chem 70:10619-37 |
Tan, Derek S; Dudley, Gregory B; Danishefsky, Samuel J (2002) Synthesis of the functionalized tricyclic skeleton of guanacastepene A: a tandem epoxide-opening beta-elimination/knoevenagel cyclization. Angew Chem Int Ed Engl 41:2185-8 |
Lin, Songnian; Dudley, Gregory B; Tan, Derek S et al. (2002) A stereoselective route to guanacastepene A through a surprising epoxidation. Angew Chem Int Ed Engl 41:2188-91 |
Dudley, G B; Danishefsky, S J (2001) A four-step synthesis of the hydroazulene core of guanacastepene. Org Lett 3:2399-402 |