795278-08-9

Upstream product

• 81805-98-3 3-Hydroxy-4,5-(methylenedioxy)benzaldehyde 

Downstream Products

• 852123-16-1 ((1S,2S,3S)-4-(4-(benzyloxy)benzo[d][1,3]dioxol-6-yl)-1-(5-bromo-4-methoxybenzo[d][1,3]dioxol-6-yl)-2,3-dimethylbutoxy)(tert-butyl)dimethylsilane 
• 181701-06-4 interiotherin A 

Relevant academic research and scientific papers

Total synthesis of the eupomatilones

(Chemical Equation Presented) Full details of the total syntheses of five members of the eupomatilone family of lignans are reported.

Asymmetric total synthesis of dibenzocyclooctadiene lignan natural products

Full details of the asymmetric total syntheses of the dibenzocyclooctadiene lignans interiotherin A, angeloylgomisin R, gomisin O, and gomisin E (epigomisin O) are presented. The syntheses were based on a unified synthetic strategy involving a novel crotylation using the Leighton auxiliary that occurred with excellent asymmetric induction (>98:2 enantiomeric ratio), a diastereoselective hydroboration/Suzuki-Miyaura coupling reaction sequence, and an atropdiastereoselective biarylcuprate coupling, both of which occurred with total (>20:1) stereocontrol. The syntheses were achieved in six to eight steps from simple aromatic precursors.

Total synthesis of eupomatilones 4 and 6: Structurally rearranged and atropisomerically fluxional lignan natural products

(Chemical Equation Presented) A convergent and diastereocontrolled total synthesis of eupomatilones 4 and 6 is reported and was based on a diastereoselective hydroboration/ oxidation sequence and a convergent Lipshutz biarylcuprate cross-coupling reaction. The structure of eupomatilone 6 is revised.