140870-58-2

Upstream product

• 85272-31-7 di-tert-butylsilyl bis(trifluoromethanesulfonate) 
• 623-36-9 (E)-2-methylpent-2-enal 
• 140870-56-0 (2R,4R,5S,6E)-5-hydroxy-2,4,6-trimethyl-1-phenylmethoxy-6-nonen-3-one 
• 140870-57-1 (2S,3S,4S,5S,6E)-2,4,6-trimethyl-1-phenylmethoxy-6-nonene-3,5-diol 
• 140889-07-2 (2R,3S,4S,5S,6E)-2,4,6-trimethyl-3,5-<dioxy>-1-phenylmethoxy-6-nonene 

Downstream Products

• 87697-98-1 Denticulatin A 

Relevant academic research and scientific papers

Total synthesis of (-)-denticulatins A and B using efficient methods of acyclic stereocontrol

The total synthesis of (-)-denticulatin B (2) was achieved in 9 steps (20% yield), with 70% overall diastereoselectivity, starting from the ethyl ketone (R)-9. Most of the stereochemistry was introduced by substrate-based control. Key steps include the boron-mediated aldol/reduction, 9 → 22, the titanium-mediated aldol-coupling. 26 + 8 → 38, and the directed cyclisation, 35 → 2. Epimerisation at C10 in 35 led to (-)-denticulatin A (1).

Studies in Polypropionate Synthesis: Stereoselective Synthesis of (-)-Denticulatins A and B.

(-)-Denticulatin B (2) was prepared in 9 steps (20percent yield) with 70percent overall ds starting from the ethyl ketone (R)-8.Key steps are the novel boron-mediated aldol/reduction, 8 -> 12, the titanium aldol coupling, 6 + 5 -> 18, and the HF-pyridine cyclisation, 20 -> 2.Epimerisation at C10 in 20 led to (-)-denticulatin A (1).