Total synthesis of the enantiomer of the furanocembrane rubifolide

摘要

The total synthesis of 57, the enantiomer of the marine furanocembrane rubifolide (3), is described starting from (S)-(-)-perillyl alcohol (5). The successful route proceeded by oxidative cleavage of 5 to ester aldehyde 30 which was protected, reduced, and homologated to the acetylene 34, the left-hand segment of the synthetic target. Addition to the right-hand aldehyde 39 afforded alcohol 40. The carbonate derivative 41 was converted to the allenylstannane aldehyde 44, which cyclized upon treatment with HF_3.Oet_2.