207276-51-5

Upstream product

• 106450-92-4 R-3,5-O-benzylidene-D-arabinose diethyl dithioacetal 
• 207276-50-4 (2R,4aR,8S,8aR)-8-(Bis-ethylsulfanyl-methyl)-2-phenyl-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxine 

Downstream Products

• 207276-52-6 (1R,5R,6R,8R)-5-((1S)-1-Hydroxy-2,2-dimethylbut-3-enyl)-8-phenyl-2,4,7,9-tetraoxabicyclo[4.4.0]decane 
• 207276-53-7 (1R,5R,6R,8R)-5-((1S)-1-Methoxy-2,2-dimethylbut-3-enyl)-8-phenyl-2,4,7,9-tetraoxabicyclo[4.4.0]decane 

Relevant academic research and scientific papers

Stereoselective synthesis of alcohols; LII: Synthesis of the C-10 to C- 18 part of the mycalamides

A synthesis of the right hand fragment, C-10 to C-18, of mycalamide B is described using three stereogenic centers of D-arabinose. This synthesis profits from the peculiar conformational properties of the trioxa-cis- decalin ring system, which has a high tendency to populate an O-proximal conformation. The described synthesis supersedes earlier attempts to reach the right hand fragment of the mycalamides from the C-10-epi-series.