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Synlett 1997; 1997(6): 734-736
DOI: 10.1055/s-1997-3268
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Total Synthesis of Prostaglandin F2α via Nickel-Promoted Stereoselective Cyclization of 1,3-Diene and Aldehyde

Yoshihiro Sato, Masanori Takimoto, Miwako Mori*
  • *Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060, Japan, FAX: +81-11-706-4982; E-mail: mori@pharm.hokudai.ac.jp
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Publication Date:
31 December 2000 (online)

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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.

prostaglandin - F2α - nickel - cyclization - 1,3-diene - aldehyde