Bipinnatin J

[1] It is one of the structurally simplest of the furanocembrenolides, and is speculated to be a biosynthetic precursor to a wide array cembrenolides along with the dehydroxylated analog, rubifolide.

[2] Although the exact biosynthesis of bipinnatin J has not been formally studied, the biosynthesis the core cembrane skeleton, neo-cembrene, has been extensively studied.

Proton elimination then yields neo-cembrene.

[3] From this point, the biosynthesis of bipinnatin J is speculative.

∆ double bond isomerization of the C7-C8 olefin then occurs to afford the Z conformation, yielding rubifolide.

Proposed biosynthesis of bipinnatin J