216174-77-5

Upstream product

• 94424-88-1 (2R,3R)-3-(ethyloxiran-2-yl)methanol 
• 216174-78-6 (2S,3R)-6-tert-butyldimethylsilyloxy-3-ethyl-2-hydroxy-4-hexynyl benzoate 
• 216174-61-7 (2S,3R,4Z)-6-tert-butyldimethylsilyloxy-3-ethyl-2-hydroxy-4-hexenyl benzoate 
• 216174-60-6 (2R,3R)-2,3-epoxypentyl benzoate 
• 1576-96-1 (E)-2-penten-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 216174-76-4 (2S,3R,4Z)-6-tert-butyldimethylsilyloxy-3-ethylhex-4-ene-1,2-diol 

Downstream Products

• 151519-02-7 pironetin 
• 668470-26-6 (2S,3R,4Z)-2,6-bis-tert-butyldimethylsilyloxy-3-ethyl-4-hexenyl p-toluenesulfonate 

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.