1621135-47-4

Upstream product

• 824-94-2 p-methoxybenzyl chloride 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 1621135-50-9 Aalyl 3,6-dideoxy-α-D-arabinohexofuranoside 
• 1621135-51-0 allyl 3,6-dideoxy-2,5-di-O-(p-methoxybenzyl)-α-D-arabinohexofuranoside 

Downstream Products

• 1621135-52-1 (3S,5S)-3-ethynyl-5-{(R)-1-[(4-methoxybenzyl)oxy]ethyl}-1-(4-methoxyphenyl)-12,12,13,13-tetramethyl-2,6,11-trioxa-12-silatetradec-8-yne 

Relevant academic research and scientific papers

Total synthesis of the putative structure of xylarinol B

The total synthesis of the putative structure of xylarinol B is described and the need to revise its structure is demonstrated. The central benzoxepine skeleton was constructed by employing a cobalt-mediated bimolecular [2+2+2] Reppe-Vollhardt alkyne cycloaddition reaction. Mismatch! A chiral pool approach starting from D-glucose has been executed to synthesize the proposed structure of xylarinol B. A cobalt-mediated intermolecular [2+2+2]-alkyne cyclotrimerization reaction is a key step to construct the central seven-membered benz-2-oxepine core (see picture; TBS=tert-butyldimethylsilyl ether, PMB=p-methoxylbenzyl ether). The spectral data of synthetic xylarinol B and its C5-epimer revealed that the structure of the natural product has been wrongly proposed.