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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 16.

Scheme 16

Auxiliary-based synthesis of the HI-ring fragment 12. Reagents and conditions: a) 104,83 LiAlH4, THF, 0 °C, 95%; b) TsCl, Et3N, CH2Cl2, 0 °C to RT, 95%; c) NaN3, TBAI, DMF, 60 °C, 93%; d) (COCl)2, DMSO, Et3N, CH2Cl2, −78 °C to RT, 95%. See ref31 for abbreviations.