Capnellane sesquiterpenes. Total synthesis of epiprecapnelladiene and Δ8(9)-capnellene
- 31 December 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 1913-1917
- https://doi.org/10.1039/p19830001913
Abstract
The total synthesis of epiprecapnelladiene(29) containing an uncommon bicyclo[6.3.0]undecane carbon skeleton is described. The fused 5,8-ring system in (29) is elaborated in a single step, using a highly regio- and stereo-selective intramolecular photocycloaddition reaction from the enol benzoate(16a). The relative stereochemistry of precapnelladiene, from the soft coral Capnella imbricata, is established as that in formula (30). In a biogenetically patterned synthesis, treatment of epiprecapnelladiene(29) or its exo-methylene isomer(28), with boron trifluoride–diethyl ether is shown to lead to Δ8(9)-capnellene(32), accompanied by smaller amounts of the positional isomers (33) and (34).Keywords
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