288092-47-7Relevant academic research and scientific papers
Synthetic studies directed toward the phorboxazoles: Preparation of the C3-C15 bisoxane segment and two stereoisomers
Greer, Patrick B.,Donaldson, William A.
, p. 6009 - 6018 (2007/10/03)
A synthetic approach to the C3-C15 segment of the cytotoxic marine metabolite phorboxazoles is described. This segment consists of a methylene linked bisoxane structure. The first pyran ring was constructed by a Lewis acid catalyzed diene-aldehyde cyclocondensation. The β-C-glucoside substitution pattern of this ring was established by a stereoselective allylation. Ozonolysis of vinyl group and enantioselective allylation of the racemic aldehyde generated two separable homoallylic alcohols (-)-22 and (+)-23. The Mosher's esters of each alcohol were determined to be >90% de. Reaction of (-)-22 with acryloyl chloride, followed by ring closing metathesis gave the dihydro-2-pyrone target (-)-5. Mitsunobu inversion of (+)-23 with p-nitrobenzoic acid, hydrolysis, and esterification with acryloyl chloride and ring closing metathesis gave pseudoenantiomeric segment (+)-6.
Phorboxazole synthetic studies: The C3-C15 bis-oxane segment
Greer, Patrick B.,Donaldson, William A.
, p. 3801 - 3803 (2007/10/03)
The enantioselective synthesis of the C3-C15 bis-oxane segment of the phorboxazoles has been accomplished from 3-t-butyldiphenylsilyloxypropanal in 9 steps (>90% ee). (C) 2000 Elsevier Science Ltd.
