630120-24-0

Upstream product

• 630120-19-3 2-bromo-6-methoxy-4-methylphenylacetaldehyde 
• 1064653-82-2 1-Bromo-3-methoxy-2-((E)-2-methoxy-vinyl)-5-methyl-benzene 
• 133129-29-0 2-bromo-6-methoxy-4-methylbenzaldehyde 
• 124-63-0 methanesulfonyl chloride 
• 630120-22-8 2-(2-bromo-6-methoxy-4-methylphenyl)ethanol 

Downstream Products

• 630120-33-1 (3S,6R,7aR)-6-[2-(2-bromo-6-methoxy-4-methylphenyl)ethyl]-7a-isobutyl-3-isopropyl-6-methyltetrahydropyrrolo[2,1-b]oxazol-5-one 
• 630120-32-0 (3S,7aR)-6-[2-(2-bromo-6-methoxy-4-methylphenyl)ethyl]-7a-isobutyl-3-isopropyltetrahydropyrrolo[2,1-b]oxazol-5-one 
• 630120-27-3 1-bromo-2-(2-iodoethyl)-3-methoxy-5-methylbenzene 

Relevant academic research and scientific papers

Synthesis of natural (-)-hamigeran B

Alkylation of lactam 10, first with iodide 15 and then with MeI, gave mainly (18:1) lactam 18. This was converted by treatment with t-BuLi and then with aqueous base into enone 4, which was elaborated into (-)-hamigeran B. A key feature of the last part of the synthesis is the use of t-BuMe 2Si-groups (as in intermediate 24) both to direct hydrogenation from the appropriate face and to protect the benzylic C-O bond from hydrogenolysis.