Tetrahedron p. 81 - 90 (1988)
Update date:2022-08-17
Topics:
Harde, C.
Bohlmann, F.
Starting with 6-methoxytetralone the unusual diterpene 3α-hydroxy-5β,10β-epoxychiliolide(15a) has been synthesized via methyl<1α,2α>-1,2,3,4,5,6,7,8-octahydro-6-oxo-1-(2-propenyl)-2,5,5-trimethyl-1-naphthoate (9) which by boranate reduction gave the desired α-hydroxy derivative.Oxidative degradation of the propenyl side chain afforded the aldehyde 11a which could be transformed to the racemic furan diterpene 15a by reaction with 3-lithiumfuran followed by lactonization and epoxidation.Similar the epimeric compound 15b, 15c and 15d were synthesized which allowed a final proof of the proposed relative stereochemistry of the six chiral centers of the natural compound.
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