61218-06-2Relevant 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
Sato,Takimoto,Mori
, p. 1753 - 1760 (2007/10/03)
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
Sato, Yoshihiro,Takimoto, Masanori,Mori, Miwako
, p. 734 - 736 (2007/10/03)
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.
A Divergent Entry into Prostaglandin Synthesis through 1,4-Addition of Methoxy(phenylthio)(trimethylsilyl)methyllithium to 4-Siloxy-2-cyclopentenone
Otera, Junzo,Niibo, Yoshihisa,Nozaki, Hitosi
, p. 3655 - 3658 (2007/10/02)
1,4-Addition of methoxy(phenylthio)(trimethylsilyl)methyllithium to 4-siloxy-2-cyclopentenone followed by in situ alkylation of the resulting enolate provides a versatile intermediate for synthesis of prostaglandins.
Prostaglandins. 2. Synthesis of Prostaglandin F2α in Optically Active Form from Chiral Precursors
Johnson, Francis,Paul, K.G.,Favara, Duccio,Ciabatti, Romeo,Guzzi, Umberto
, p. 2190 - 2198 (2007/10/02)
A synthetic route to optically active prostaglandins is described which use chiral starting materials.Acylation of the bis(magnesiobromide) salt of methyl hemimalonate with (S)-(-)-2-acetoxysuccinyl chloride led to unstable dimethyl (S)-4-acetoxy-3,6-diox
PROSTAGLANDIN ANALOGUES: Δ15,16-17-Hydroxy-21,22-dihomo(DHPG3.s)
Ciabatti, Romeo,Guzzi, Umberto,Fazio, Ezio
, p. 181 - 186 (2007/10/02)
The synthesis of Δ15,16-17-hydroxy-21,22-dihomo PG3.s (DHPG3) is reported.The key step is the condensation of the α,β-unsaturated aldehyde 3 with the phosphonate 12.The configuration of the 17-hydroxyl group was assigned by analogy of the chromatographic behaviour of DHPG3.s with the natural PG.s.
Prostaglandin Analogues Possessing Antinidatory Effects. 2. Modification of the α Chain
Hayashi, Masaki,Arai, Yoshinobu,Wakatsuka, Hirohisa,Kawamura, Masanori,Konishi, Yoshitaka,et al.
, p. 525 - 535 (2007/10/02)
Additional double bonds were introduced into the α chain in 16-phenoxy-, 16-(3-chlorophenoxy)-, 16--, and 16-(4-chlorophenoxy)-17,18,19,20-tetranorprostaglandins which have antinidatory effects.Of these analogues, the Δ3/
