Therefore,
we proposed the synthesis of 7-methoxytetradec-4-enoic acid
to be achieved by the Julia–Lythgoe olefination strategy. Hermitamides
A (1) and B (2) could be cleaved into two main fragments,
that is, alkyl sulfone 10 and aldehyde 14. Chiral alkyl sulfone 10
could be conveniently prepared from methoxy alcohol 8. The chiral
center of the key intermediate 10 can be generated from the CBS
reduction of 6, followed by methylation of the hydroxyl group
and subsequent hydroboration of the terminal olefin. Compound
6 could easily be obtained from n-octanal 4 through vinylation followed
by oxidation of allylic alcohol 5.