1621135-58-7

Upstream product

• 824-94-2 p-methoxybenzyl chloride 
• 58475-17-5 (R)-1-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethan-1-ol 
• 1621135-57-6 (2R,3S,5R)-2,5-bis((4-methoxybenzyl)oxy)hept-6-yn-3-ol 
• 219996-95-9 tert-butyl((4-iodobut-2-yn-1-yl)oxy)dimethylsilane 
• 1621135-56-5 allyl 3,6-dideoxy-2,5-di-O-(p-methoxybenzyl)-β-D-ribohexofuranoside 
• 1621135-55-4 allyl 3,6-dideoxy-β-D-ribohexofuranoside 

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.