315716-40-6

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 193476-26-5 methyl (5Z)-7-[(1R,2S,3R,5R)-5-acetoxy-2-(tert-butyldiphenylsilyloxymethyl)-3-hydroxycyclopentyl]-5-heptenoate 
• 377778-93-3 5-((tert-butyldimethylsilyl)oxy)pent-2-en-1-ol 
• 86462-75-1 (E)-5-(tert-butyldimethylsilanyloxy)pent-2-en-1-ol 
• 315716-36-0 (1R,6S,7R,8S)-8-tert-butyldimethylsilyloxy-3,3-dimethyl-2,4-dioxa-7-(2-propenyl)-bicyclo[4.3.0]nonan-8-ol 
• 193476-16-3 (2E)-3-[(1S,2R)-2-(2-tert-butyldimethylsilyloxyethyl)-4,4-dimethyl-3,5-dioxacyclohexyl]-2-propen-1-ol 
• 193476-17-4 (4R,5S)-4-{5-[(1E)-1,3-butadienyl]}-4-(2-tert-butyldimethylsilyloxyethyl)-2,2-dimethyl-1,3-dioxa-cyclohexane 
• 193476-14-1 (4R,5S)-4-(2-tert-butyldimethylsilyloxyethyl)-2,2-dimethyl-1,3-dioxa-5-ethenylcyclohexane 
• 315716-32-6 2-{(1R,6S)-6-[(1E)-1,3-butadienyl]-3,3-dimethyl-2,4-dioxacyclohexyl}ethanol 
• 193476-19-6 (1R,6S,7R,8S)-3,3-dimethyl-2,4-dioxa-7-(2-propenyl)bicyclo[4.3.0]nonan-8-ol 
• 193476-13-0 (2S,3R)-5-tert-butyldimethylsilyloxy-2-ethenylpentan-1,3-diol 
• 193476-18-5 2-{(1R,6S)-6-[(1E)-1,3-butadienyl]-3,3-dimethyl-2,4-dioxacyclohexyl}ethanal 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 136235-73-9 (2R,3S)-5-tert-butyldimethylsilyloxy-2,3-epoxypentan-1-ol 

Downstream Products

• 61218-10-8 methyl (5Z)-7-{(1R,2S,3R,5R)-5-acetoxy-2-hydroxymethyl-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate 
• 551-11-1 dinoprost 
• 55022-57-6 methyl (5Z)-7-{(1R,2R,3R,5R)-5-acetoxy-3-hydroxy-2-[(1E,3S)-3-hydroxy-1-octenyl]cyclopentyl}-5-heptenoate 
• 61218-06-2 methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate 
• 33854-16-9 (+)-prostaglandin F_2α 

Relevant academic research and scientific papers

Total Synthesis of Prostaglandin F2α via Nickel-Promoted Stereoselective Cyclization of 1,3-Diene and Aldehyde

The total synthesis of prostaglandin F2α (PGF2α) was accomplished via nickel-promoted cyclization of 1,3-diene and aldehyde in a chain in the presence of 1,3-cyclohexadiene (1,3-CHD). The cyclization of 16 prepared in an optically active form from chiral epoxy alcohol 10 stereoselectively gave the key intermediate 18, which has both an α-chain and the four contiguous chiral carbon centers in PGF2α, in a one-pot reaction. Intermediate 18 was successfully transformed into PGF2α.

Total synthesis of prostaglandin F(2α) using nickel-catalyzed stereoselective cyclization of 1,3-diene and tethered aldehyde via transmetalation of nickelacycle with diisobutylaluminum acetylacetonate

Total synthesis of prostaglandin F(2α) utilizing a nickel(0)-catalyzed cyclization of 1,3-diene and tethered aldehyde was achieved. The cyclization proceeded via a transmetalation of nickelacycle with dilsobutylaluminum acetylacetonate ((i)Bu2-ALAC). Thus, the reaction of 19, having a side chain corresponding to the α-chain in PGF(2α) with Ni(cod)2 (10 mol %), PPh3 (20 mol %), and 1,3-cyclohexadiene (25 mol %) in the presence of (i)Bu2-ALAC (1.5 eq) proceeded stereoselectively to give the cyclized product 26 in 54% yield. During the cyclization of 19, the Z-olefin at C-5 in the side chain completely retained its geometry, and the four contiguous chiral carbon centers in PGF(2α) were stereoselectively constructed. Transformation of the key intermediate 19 into PGF(2α) was successfully achieved.