61218-10-8Relevant articles and documents
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 (2000)
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.
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/