123284-71-9

Upstream product

• 917-54-4 methyllithium 
• 104322-42-1 (-)-(2S)-benzyloxy-2,5-dihydrofuran-4-carboxaldehyde 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 104322-41-0 (+)-(2R)-benzyloxy-2,5-dihydrofuran-4-carboxaldehyde 

Downstream Products

• 113466-43-6 (+)-(2R,3S,4S)-2-benzyloxy-4-<(1RS)-1-hydroxyethyl>-3-methyltetrahydrofuran 
• 113466-43-6 1-((3S,4S,5R)-5-Benzyloxy-4-methyl-tetrahydro-furan-3-yl)-ethanol 
• 114286-20-3 (+)-(2R,3S,4R)-4-acetyl-2-benzyloxy-3-methyltetrahydrofuran 
• 113466-50-5 (+)-(2R,3S,4S)-4-acetyl-2-benzyloxy-3-methyltetrahydrofuran 
• 113466-41-4 (2R,3S,4S)-2-benzyloxy-4-formyl-3-methyltetrahydrofuran 
• 113466-42-5 (2R,3S,4R)-2-benzyloxy-4-formyl-3-methyltetrahydrofuran 
• 113466-43-6 (2R,3S,4SR)-2-benzyloxy-4-(1-hydroxyethyl)-3-methyltetrahydrofuran 
• 27098-03-9 (-)-epi-botryodiplodin 
• 27098-03-9 (+)-botryodiplodin 
• 113466-39-0 (+)-(2R,3S,4SR)-2-benzyloxy-4-formyl-3-methyltetrahydrofuran 

Relevant academic research and scientific papers

Total Synthesis of (-)- and (+)-Botryodiplodin and (+)- and (-)-Epibotryodiplodin

the title compounds were prepared by the conjugate addition (d.e. more than 94percent) of LiMeCNCu to the chiral isoprene units (+)-(2R)- and (-)-(2S)-benzyloxy-2,5-dihydrofuran-4-carboxaldehyde (1r and 1s) followed by methyllithium-attack on the mixture

DIASTEREOSELECTIVE CONJUGATE ADDITION OF LITHIUM METHYLCYANOCUPRATE TO THE CHIRAL ISOPRENE UNITS 2-(R)- AND (S)-BENZYLOXY-2,5-DIHYDRO-4-FURANCARBOXALDEHYDE. TOTAL SYNTHESIS OF (-)- AND (+)-BOTRYODIPLODIN AND (+)- AND (-)-EPIBOTRYODIPLODIN.

Conjugate addition of lithium methylcyanocuprate to the title aldehydes proceeded with high diastereoselectivity (d.e. 94percent).Methyl lithium 1,2-addition, followed by Swern oxidation of the resulting alcohols, gave benzyl botryodiplodin and benzyl epi