184827-13-2

Upstream product

• 100-39-0 benzyl bromide 
• 184827-12-1 5,6-dihydro-7-hydroxy-5H-[2]pyrindin-7-one 
• 184827-10-9 1-hydroxy-4-methylenocyclopentano[2,3-c]pyridine 
• 70201-43-3 3-bromo-pyridine-4-carbaldehyde 
• 184827-09-6 3-bromo-4-(but-3-yn-1-ol)pyridine 
• 160540-47-6 4-(1-benzyloxy-2-hydroxy)-3-trimethylsilylethynylpyridine 
• 160540-48-7 4-(1-benzyloxy-2-hydroxy)-3-ethynylpyridine 
• 160540-44-3 3-bromo-4-(2-tetrahydropyranyloxyacetyl)pyridine 
• 626-55-1 3-Bromopyridine 
• 872-85-5 pyridine-4-carbaldehyde 
• 160540-49-8 4-(1-benzyloxy-2-bromo)-3-ethynylpyridine 

Downstream Products

• 160540-51-2 1-benzyloxy-4-oxocyclopentano<2,3-c>pyridine 

Relevant academic research and scientific papers

Pyridine radicals in synthesis. Part 3: Cyclopentannulation of pyridine via the 3-pyridyl radical and a formal synthesis of (±)-oxerine

The allylation and propargylation of 3-bromo-4-formylpyridine under zinc-mediated Barbier conditions is described. The homoallylic alcohols produced are cyclised via the derived 3-pyridyl radical to give cyclopentannulated pyridines. One of these bicyclic compounds is converted into an advanced intermediate in a previous synthesis of the monoterpene alkaloid (±)-oxerine. (C) 2000 Elsevier Science Ltd.

Pyridine radicals in synthesis: A formal total synthesis of (±)-oxerine

The cyclisation of pyridine radicals derived from 3-bromo-4-substituted pyridines carrying both alkene and alkyne groups in the 4-substituent to give is described. The cyclopentano[c]pyridine skeleton formed by cyclisation is found in many monoterpene alkaloids and a short synthesis of a late intermediate in the previous synthesis of (±)-oxerine is presented.

First Total Synthesis of (+/-)-Oxerine

Total synthesis of (+/)-oxerine (1), a monoterpene alkaloid, starting from 3-bromopyridine (7) is described.The key reaction in this sequence is the samarium iodide (SmI2)-mediated intramolecular cyclization of γ-ethynyl bromide (4).