171014-90-7

Upstream product

• 184868-93-7 5-Benzyloxymethyl-4-methyl-furan-2-carboxylic acid 
• 20416-16-4 (3-methylfuran-2-yl)methanol 
• 6141-57-7 methyl 3-methylfuran-2-carboxylate 
• 130446-62-7 5-Hydroxymethyl-4-methyl-furan-2-carboxylic acid 
• 184868-94-8 5-Benzyloxymethyl-4-methyl-furan-2-carboxylic acid benzyl ester 

Downstream Products

• 184868-99-3 (1S,2R,6S,8R)-8-Benzyloxymethyl-6,9-dimethyl-2-trityloxymethyl-12-oxa-tricyclo[6.3.1.0^1,6]dodec-9-en-11-one 
• 184868-98-2 Acetic acid 2-benzyloxymethyl-3-methyl-6-((R)-5-methyl-1-trityloxymethyl-hex-5-enyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl ester 
• 184869-02-1 (1S,2R,6S,8R,10R)-8-Benzyloxymethyl-6,9,9-trimethyl-10-(2-nitro-butyl)-2-trityloxymethyl-12-oxa-tricyclo[6.3.1.0^1,6]dodecan-11-one 
• 184868-97-1 6-Benzyloxymethyl-6-hydroxy-5-methyl-2-((R)-5-methyl-1-trityloxymethyl-hex-5-enyl)-6H-pyran-3-one 
• 184868-96-0 (R)-1-(5-Benzyloxymethyl-4-methyl-furan-2-yl)-6-methyl-2-trityloxymethyl-hept-6-en-1-ol 
• 184869-01-0 (1S,2R,6S,8R)-8-Benzyloxymethyl-6,9,9-trimethyl-10-methylene-2-trityloxymethyl-12-oxa-tricyclo[6.3.1.0^1,6]dodecan-11-one 
• 184869-00-9 (1S,2R,6S,8R)-8-Benzyloxymethyl-6,9,9-trimethyl-2-trityloxymethyl-12-oxa-tricyclo[6.3.1.0^1,6]dodecan-11-one 
• 184869-03-2 (1S,2R,6S,8R,10R)-8-Benzyloxymethyl-2-hydroxymethyl-6,9,9-trimethyl-10-(2-nitro-butyl)-12-oxa-tricyclo[6.3.1.0^1,6]dodecan-11-one 
• 184869-13-4 (-)-4α-formyl-8β,11,11-trimethyl-10β-benzyloxymethyl-3α,10α-oxido-1,2-(2-ethoxypyranenyl)-bicyclo[5.4.0^3,8]undecane 
• 184869-05-4 (1S,2S,6S,8R,10R)-8-Benzyloxymethyl-6,9,9-trimethyl-11-oxo-10-(2-oxo-butyl)-12-oxa-tricyclo[6.3.1.0^1,6]dodecane-2-carbaldehyde 
• 184869-12-3 (-)-4α-hydroxymethyl-8β,11,11-trimethyl-10β-benzyloxymethyl-3α,10α-oxido-1,2-(2-ethoxypyranenyl)-bicyclo[5.4.0^3,8]undecane 
• 184869-04-3 (1S,2R,6S,8R,10R)-8-Benzyloxymethyl-2-hydroxymethyl-6,9,9-trimethyl-10-(2-oxo-butyl)-12-oxa-tricyclo[6.3.1.0^1,6]dodecan-11-one 
• 184869-11-2 (1S,2R,6S,8R)-8-Benzyloxymethyl-2-hydroxymethyl-6,9,9-trimethyl-10-methylene-12-oxa-tricyclo[6.3.1.0^1,6]dodecan-11-one 
• 184868-95-9 2-[2-(5-benzyloxymethyl-4-methylfuryl)-2-hydroxymethyl]-6-methyl-6-hepten-1-ol 

Relevant academic research and scientific papers

Taxane diterpenes 3: Formation of the eight-membered B-ring by semi-pinacol rearrangement

The substituted furan carboxaldehyde 15 was converted into enone 20 via a stereoselective intramolecular pyrylium ylide-alkene cyclization. Subsequent elaboration of 20 into the triflate 23, followed by solvolysis in acidic trifluoroethanol resulted in quantitative rearrangement to the taxane B/C core 24. At a higher oxidation level 27 was ring expanded to give 28. The ring expanson strategy could also be initiated by β-elimination of the 3α,10α-oxido bridge. Treatment of 50 with MeOH at reflux gave 52. Similar transformations in the 7-oxy series resulted in ring B expansion of 67 to give 68, and 75 to give 76.