Synthesis of Aromatic Diterpenes Synthesis of 12-Hydroxy-abieta-8,11,13-trien-3,7-dione

References

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• The conditions and yields for the lettered reactions in the drawings were: (a) CH3COCl,AlCl3, CH2CL2, r.t., 8 h: 78%. (b) CH3MgI, ether, 5°C :85%. (c) glac. HOAc, reflux, 2 h: 100%. (d) H2, Pd/C, 40 psi, ether: 99%. (e) PCC, HOAc, Celite, Molecular sieve 4Å, CH2Cl2: 75% counting the recovered starting material. (f) The primary acetate was first hydrolysed with NaOH in MeOH/H2O at r.t. for 2h (100%) then i) NH2OH.HCl, NaOH, EtOH/H2O, r.t., 4 h ii) Ac2O, reflux, 4 h:57%. (g) KBr, 18-cr-6, m-CPBA, CH2Cl2, 0°C, 30 min: 84%. (h) Mg, THF then DMF: 98%. (i) NaBH4, MeOH, r.t., 12 min: 97%. (j) PBr3, pyr, benzene, r.t., 3 h: 98%. (k) KCN, 18-cr-6, CH3CN, 60°, 1 h:80%. (l) LDA, THF,-78°C then add 9, r.t., 3 h :85%. (m) See Experimental Section (n) i) LDA, THF,-78°C, bubble O2, 1 h ii) 1M SnCl2 in 2M HCl, 0°C : 55%. (o) m-CPBA, CH2Cl2,-78°C : 92%. (p) Trifluoroacetic anhydride, pyr, CH2Cl2, 0°C, 5 h :72%. (q) glac. HOAc, TiCl4, r.t., 20 min ii) H2O, reflux, 1 h: 93%. (r) BBr3, CH2Cl2, 0°C rising to r.t. overnight: 91%
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