193476-26-5

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 86462-75-1 (E)-5-(tert-butyldimethylsilanyloxy)pent-2-en-1-ol 
• 377778-93-3 5-((tert-butyldimethylsilyl)oxy)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 
• 136235-73-9 (2R,3S)-5-tert-butyldimethylsilyloxy-2,3-epoxypentan-1-ol 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 193476-20-9 methyl (5Z,7E)-8-[(1S,2R)-2-(2-tert-butyldimethylsilyloxyethyl)-4,4-dimethyl-3,5-dioxacyclohexyl]-5,7-octadienoate 

Downstream Products

• 315716-40-6 methyl (5Z)-7-[(1R,2S,3R,5R)-5-acetoxy-2-(tert-butyldiphenylsilyloxymethyl)-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 
• 61218-10-8 methyl (5Z)-7-{(1R,2S,3R,5R)-5-acetoxy-2-hydroxymethyl-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate 
• 33854-16-9 (+)-prostaglandin F_2α 

Relevant academic research and scientific papers

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.

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.