Syntheses of poly‐deuterated 9( O )‐methano‐Δ 6(9α) ‐prostaglandin I 1 methyl esters

Two types of poly‐deuterated isocarbacyclin [9( O )‐methano‐Δ 6(9α) ‐prostaglandin I 1 ] methyl ester have been synthesized for the use of GC‐MS quantitative analysis as internal standards and for the use of metabolic study as substrates. The 5,13,14‐ 2 H 3 derivative 2 was prepared via H‐D exchange, deuteroboration, and sodium borodeuteride reduction. The 2,2,3,3,4,4‐ 2 H 6 derivatives 3 , 4 were prepared starting from tetrahydrofuran‐d 8 .