(1R,3S,8R)-3,7,7,10-Tetra­methyl­tri­cyclo­[6.4.0.0^1,3]dodec-9-en-11-one

The absolute configuration of the title compound, C₁₆H₂₄O, has been deduced from the chemical pathway. The six-membered ring has a roughly half-chair conformation with the quaternary C atom as the flap. The seven-membered ring displays a chair conformation. In the crystal, there is a weak C—H...O hydrogen bond between the methyl­ene group of the cyclo­propane ring and the carbonyl group of a screw-axis-related mol­ecule, which builds up a zigzag-like chain along the b-axis direction.

(4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octa­hydro­phenan­thren-2-yl acetate

The hemisynthesis of the title compound, C₂₂H₃₂O₂, was carried out through direct acetyl­ation reaction of the naturally occurring diterpene totarol [systematic name: (4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexa­hydro­phen­an­thren-2-ol]. The mol­ecule is built up from three fused six membered rings, one saturated and two unsaturated. The central unsaturated ring has a half-chair conformation, whereas the other unsaturated ring displays a chair conformation. The absolute configuration is deduced from the chemical pathway. The value of the Hooft parameter [-0.10 (6)] allowed this absolute configuration to be confirmed.

(4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octa­hydro­phenan­thren-2-yl acetate

The hemisynthesis of the title compound, C₂₂H₃₂O₂, was carried out through direct acetyl­ation reaction of the naturally occurring diterpene totarol [systematic name: (4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexa­hydro­phen­an­thren-2-ol]. The mol­ecule is built up from three fused six membered rings, one saturated and two unsaturated. The central unsaturated ring has a half-chair conformation, whereas the other unsaturated ring displays a chair conformation. The absolute configuration is deduced from the chemical pathway. The value of the Hooft parameter [-0.10 (6)] allowed this absolute configuration to be confirmed.

(1S,3S,8R,9S,10R)-9,10-Ep­oxy-3,7,7,10-tetra­methyl­tri­cyclo­[6.4.0.0^1,3]dodeca­ne

The title compound, C₁₆H₂₆O, was synthesized by treating (1S,3S,8R)-3,7,7,10-tetra­methyl­tri­cyclo­[6.4.0.0^1,3]dodec-9-ene with meta­chloro­perbenzoic acid. The mol­ecule is built up from two fused six- and seven-membered rings. The six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a boat conformation. In the crystal, there are no significant intermolecular interactions present.

(1S,3S,8R,9S,10R)-9,10-Ep­oxy-3,7,7,10-tetra­methyl­tri­cyclo­[6.4.0.0^1,3]dodeca­ne

The title compound, C₁₆H₂₆O, was synthesized by treating (1S,3S,8R)-3,7,7,10-tetra­methyl­tri­cyclo­[6.4.0.0^1,3]dodec-9-ene with meta­chloro­perbenzoic acid. The mol­ecule is built up from two fused six- and seven-membered rings. The six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a boat conformation. In the crystal, there are no significant intermolecular interactions present.

(4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octa­hydro­phenan­thren-2-yl benzoate

The title compound, C₂₇H₃₄O₂, was hemisynthesized through direct benzoyl­ation of the naturally occurring meroterpene totarol. The central fused six-membered ring has a half-chair conformation, whereas the terminal six-membered ring displays a chair conformation. The dihedral angle between the fused benzene ring and the benzoyl benzene ring is 73.05 (14)°. The S,S chirality of the mol­ecule is consistent with the synthetic pathway, and confirmed by the refinement of the Flack parameter.

(4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octa­hydro­phenan­thren-2-yl benzoate

The title compound, C₂₇H₃₄O₂, was hemisynthesized through direct benzoyl­ation of the naturally occurring meroterpene totarol. The central fused six-membered ring has a half-chair conformation, whereas the terminal six-membered ring displays a chair conformation. The dihedral angle between the fused benzene ring and the benzoyl benzene ring is 73.05 (14)°. The S,S chirality of the mol­ecule is consistent with the synthetic pathway, and confirmed by the refinement of the Flack parameter.