Methyl 4-pentynoate → HCID 11742322, compound

Participants

Reaction Steps

The synthesis of the acid 41 and 65 is published in J. Med. Chem. 1986 Vol. 29, p. 2300. The acids 45, 63, and 64 were prepared by the reaction sequence detailed in Example 226. Palladium catalyzed coupling of the Δ16 -17-triflate 60 with methyl 4-pentynoate using the procedures published in Synlett. 1991 p. 409; J. Org. Chem. 1992 Vol. 57, p. 973. gave the enyne 61. Hydrogenation catalyzed with palladium on carbon formed the saturated ester 62 and KOH saponification gave 45. Similar reaction sequences using methyl 5-hexynoate and 10-undecynoic acid gave the acids 63 and 64.

Provenance & Evidence