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

Author:

Burnell Robert H.,Caron Stéphane

Publisher

Informa UK Limited

Subject

Organic Chemistry

Reference12 articles.

1. Candelabrone, a new abietane diterpene from the leaves of Salvia candelabrum

2. Caesalpin F: A New Furanoditerpene from Caesalpinia bonducella

3. Ph. D. Thesis;Côté C.,1988

4. 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 SnCl2in 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%

5. Sulfenium ion promoted polyene cyclizations in natural product synthesis

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