288092-41-1

Upstream product

• 54125-02-9 danishefsky's diene 
• 112897-03-7 3-(tert-butyldiphenylsilyloxy)-1-propanal 

Downstream Products

• 288092-46-6 Acetic acid (2S,4R,6S)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-4-yl ester 
• 468757-09-7 Acrylic acid (S)-1-{(2R,4S,6R)-4-acetoxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-ylmethyl}-but-3-enyl ester 
• 288092-47-7 Acrylic acid (S)-1-{(2S,4R,6S)-4-acetoxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-ylmethyl}-but-3-enyl ester 

Relevant academic research and scientific papers

Synthetic studies directed toward the phorboxazoles: Preparation of the C3-C15 bisoxane segment and two stereoisomers

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

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.