HCID 15063013, compound → HCID 57548711, compound

Participants

Reaction Steps

Another approach is shown in SCHEME III. It can be described as C16+IPhC2=IPhC18. The C16 fragment 43 originates from relatively inexpensive 16-hexadecanolactone 31. Lactone cleavage with trimethylsilyl iodide in the presence of ethanol results in ethyl 16-iodohexadecanoate 43. Iodoester 43 is coupled with organozinc reagent 44 made from 2-(p-iodophenyl)ethyl bromide to give ester 37 which has all 18 carbons chain required for NM404. Ester 37 is converted into 18-(p-iodophenyl)octadecanol 12 in two steps as shown in SCHEME III.

Provenance & Evidence