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. Author manuscript; available in PMC: 2011 Jul 12.
Published in final edited form as: Angew Chem Int Ed Engl. 2010 Jul 12;49(30):5146–5150. doi: 10.1002/anie.201002264

Scheme 5.

Scheme 5

Total synthesis of dalesconol A (1): a) KOt-Bu (1.0 M in THF, 1.1 equiv), THF, −78 °C, 20 min; 14 (1.0 equiv), −78→25 °C, 3 h, 79%; b) n-BuLi (1.6 M in hexanes, 1.5 equiv), THF, −78 °C; 18 (2.0 equiv), −78→25 °C, 4 h, 51%; c) H2 (1 atm), Pd/C (10%, 1 equiv), EtOAc/EtOH (2/3), 25 °C, 1 h; filter, solvent removal, TFA (1.0 equiv), 2,2,2-trifluoroethanol, −45 °C, 15 min; PhI(OAc) 2 (1.1 equiv), −45 °C, 20 min, 27% overall; d) H2 (1 atm), Pd/C (10%, 1.0 equiv), EtOH/EtOAc (3/1), 25 °C, 3–10 h, 65%; e) conc. HCl (30 equiv), THF, 0→25 °C, 2 h, 99%; f) DDQ (1.1 equiv), benzene, 25 °C, 30 min, 77%; g) Pd(OAc)2 (1.0 equiv), t-BuOOH (25 equiv), K2CO3 (10 equiv), CH2Cl2, 72 h, 25 °C, 41%; i) Dess–Martin periodinane (5.0 equiv), NaHCO3 (10 equiv), CH2Cl2, 25 °C, 2 h, 99%; j) BBr3 (1.0 M in CH2Cl2, 15 equiv), CH2Cl2, −78→25 °C, 5 h, 66%.