216174-61-7

Upstream product

• 129588-82-5 C₁₂H₂₆AlOSi^(1-)*Li⁽¹⁺⁾ 
• 216174-60-6 (2R,3R)-2,3-epoxypentyl benzoate 
• 94424-88-1 (2R,3R)-3-(ethyloxiran-2-yl)methanol 
• 1576-96-1 (E)-2-penten-1-ol 
• 216174-78-6 (2S,3R)-6-tert-butyldimethylsilyloxy-3-ethyl-2-hydroxy-4-hexynyl benzoate 

Downstream Products

• 668470-26-6 (2S,3R,4Z)-2,6-bis-tert-butyldimethylsilyloxy-3-ethyl-4-hexenyl p-toluenesulfonate 
• 216174-77-5 (2S,3R,4Z)-6-tert-butyldimethylsilyloxy-3-ethyl-1-p-toluenesulfonyloxy-4-hexene-2-ol 
• 151519-02-7 pironetin 
• 668470-23-3 (2S,3R,4Z)-2,6-bis-tert-butyldimethylsilyloxy-3-ethyl-4-hexenyl benzoate 

Relevant academic research and scientific papers

An efficient synthesis of pironetins employing a useful chiral building block, (1S, 5S, 6R)-5-hydroxybicyclo [4.1.0]heptan-2-one

A convergent total synthesis of pironetin 1 and related compound 2 using a chiral building block, (IS, 5S, 6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 5 is described. Both the dithiane 47 and the epoxide 32 with proper substituents were employed as coupling partners to construct the whole carbon skeleton 48, which was converted to (-)-pironetin 1 and (-)-2 in few steps. The usefulness of 5 for polyketide synthesis was demonstrated.

Total synthesis of (-)-pironetin

The convergent total synthesis of (-)-pironetin using a chiral building block, (1S, 5S, 6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 5 is described. Both the dithiane 4 and the epoxide 2 with proper substituents were employed as coupling partners to construct the whole carbon skeleton 15, which was converted to pironetin 1 in a few steps.