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. Author manuscript; available in PMC: 2012 Jul 31.
Published in final edited form as: J Am Chem Soc. 2008 Dec 3;130(48):16295–16309. doi: 10.1021/ja804659n

Scheme 19.

Scheme 19

Assembly of the EFGHI carbon skeleton and formation of the FG bicyclic ketal 115. Reagents and conditions: a) Cy2BCl (2.4 equiv), i-Pr2NEt, CH2Cl2, −78 °C, then 10 (1.4 equiv), −78 to 0 °C; then H2O2, MeOH, pH 7 buffer, 0 °C to RT, dr 60:40; b) HF, H2O, CH3CN, 0 °C, 92% (2 steps); c) Dess-Martin periodinane, pyr, CH2Cl2, 85%. See ref31 for abbreviations.