364337-19-9

Upstream product

• 364337-18-8 methyl (2R)-2-p-methoxybenzyloxy-4-phenylselanylbutanoate 
• 364337-17-7 methyl (2R)-2-hydroxy-4-phenylselanylbutanoate 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 1666-13-3 diphenyl diselenide 

Downstream Products

• 527754-96-7 (4R,5S,6S)-5-methoxy-4-p-methoxybenzyloxy-6-[(E)-1,5-dimethylhex-1-enyl]cyclohex-2-enone 
• 527754-98-9 (2S,3S,4R)-3-methoxy-4-p-methoxybenzyloxy-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone 
• 527754-94-5 (4S)-4-((1S,2R)-1-methoxy-2-p-methoxybenzyloxybut-3-enyl)-5,9-dimethyldeca-1,5-dien-3-one 
• 527755-39-1 (1R,3S,4S,5S,6R)-3-[(E)-1,5-dimethylhex-1-enyl]-4-methoxy-5-p-methoxybenzyloxy-7-oxabicyclo[4.1.0]heptan-2-one 
• 527755-34-6 (2S,3S,4R,5S)-2-((E)-1,5-dimethylhex-1-enyl)-3-methoxy-4-p-methoxybenzyloxy-5-methylcyclohexanone 
• 527754-99-0 (3R,4S,5S,6R)-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane 
• 527755-36-8 (3R,4S,5S,6R,7S)-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-6-p-methoxybenzyloxy-7-methyl-1-oxaspiro[2.5]octane 
• 527754-92-3 (2S)-2-[(1S,2R)-1-methoxy-2-p-methoxybenzyloxybut-3-enyl]-3,7-dimethylocta-3-enoic acid methoxymethylamide 
• 527754-90-1 (2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxybut-3-enyl]-3,7-dimethylocta-3-enoic acid methoxymethylamide 
• 527755-41-5 (2S,3S,4R,5S)-2-[(E)-1,5-dimethylhex-1-enyl]-5-hydroxy-3-methoxy-4-p-methoxybenzyloxycyclohexanone 
• 655253-25-1 (3R,4S,5S,6R)-4-[(1S,2S)-1,2-epoxy-1,5-dimethylhexyl]-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane 
• 655253-24-0 (3R,4S,5S,6R)-4-[(1R,2R)-1,2-epoxy-1,5-dimethylhexyl]-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane 
• 527755-49-3 (4R,5S,6S)-6-[(E)-1,5-dimethylhex-1-enyl]-2-hydroxymethyl-5-methoxy-4-p-methoxybenzyloxycyclohex-2-enone 
• 527755-43-7 (2S,3S,4S,5S)-2-[(E)-1,5-dimethylhex-1-enyl]-5-(isopropyldimethylsilanyloxy)-3-methoxy-4-p-methoxybenzyloxycyclohexanone 

Relevant academic research and scientific papers

MetAP-2 Inhibitors Based on the Fumagillin Structure. Side-Chain Modification and Ring-Substituted Analogues

The preparation of a series of new fumagillin-derived MetAP-2 inhibitors is described. The synthetic approach was designed so as to permit modification of the fumagillin backbone at sites inaccessible through semisynthesis or previously existing total syntheses. An Evans aldolization and a ring-closing metathesis allowed the preparation of a pivotal intermediate which could then be functionalized in various ways using already established or newly developed methodologies.

A new, ring closing metathesis-based synthesis of (-)-fumagillol

(Equation presented) A new strategy to access the fumagillin/fumagillol skeleton is proposed. An Evans aldolization and a RCM involving an enone are used for the preparation of a key cyclohexanone intermediate, which was readily converted to fumagillol. The synthesis also features an efficient preparation of isogeraniol and isogeranic acid.