1025908-50-2

Upstream product

• 2466-76-4 N-Acetylimidazole 
• 171012-23-0 (1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-((S)-[1,3]dithian-2-yl-hydroxy-methyl)-2,4,4-trimethyl-cyclohex-2-enol 
• 171012-35-4 1(R)-<<(1',1'-Dimethylethyl)dimethylsilyl>oxy>-3(R)-<(acetyloxy)methyl>-4(R),5(S)-oxido-2,2,4-trimethylcyclohexane 
• 171012-25-2 3(R)-<<(1',1'-Dimethylethyl)dimethylsilyl>oxy>-5(R),6(S)-oxido-2,2,6-trimethylcyclohexan-1(R)-carboxaldehyde 
• 171012-26-3 5(R)-<<(1',1'-Dimethylethyl)dimethylsilyl>oxy>-3(S)-hydroxy-2,6,6-trimethylcyclohexen-1-carboxaldehyde 
• 171012-34-3 3(R)-<(Acetyloxy)methyl>-4(R),5(S)-oxido-2,2,4-trimethylcyclohexan-1(R)-ol 
• 171012-36-5 1(R)-<<(1',1'-Dimethylethyl)dimethylsilyl>oxy>-3(R)-(hydroxymethyl)-4(R),5(S)-oxido-2,2,4-trimethylcyclohexane 
• 171231-05-3 (R,E)-((5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-yl)oxy)trimethylsilane 
• 171231-04-2 3(S)-(Hydroxymethyl)-2,2,4-trimethylcyclohex-3-en-1(R)-ol 
• 171012-24-1 3(R)-(Hydroxymethyl)-4(R),5(S)-oxido-2,2,4-trimethylcyclohexan-1(R)-ol 
• 61302-42-9 (R,E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol 

Relevant academic research and scientific papers

Taxol Total Synthesis: Preparation of a Chiral Ring A Moiety via Biomimetic Cyclization and Evaluation of a Tandem Nitrile Oxide Strategy for Rings B/C

A fully functionalized taxol ring A moiety 7 was efficiently prepared via biomimetic cation-olefin cyclization of chiral geraniol epoxide 2b using SnCl4 in toluene.Fractional crystallization provided endo-3 (50percent yield from 2b) that was converted to aldehyde 5 by stereospecific epoxidation, secondary alcohol protection, and PCC oxidation.NaOMe-mediated ring opening secured enal 6.Addition of lithium dithianne to 6 at low temperature provided 7 as the sole product in good yield.A tandem nitrile oxide cycloaddition strategy for creating the remaining B/C carbocycles as well as key functionality present in both rings was validated, in part, by cyclization of 14 to tricyclic isoxazoline 15.