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. Author manuscript; available in PMC: 2010 Jan 1.
Published in final edited form as: Angew Chem Int Ed Engl. 2009;48(32):5860–5863. doi: 10.1002/anie.200902509

Scheme 4.

Scheme 4

18O2 Studies elucidating the samarium-induced 1,3-allylic alcohol transposition reaction (15→16). Reagents and conditions: a) i. SmI2 (4.0 equiv), MeOH (10.0 equiv), THF, –78 °C, 5 min; – 78→25 °C; ii. 18O2 (balloon), 25 °C, 18 h; iii. aq. Na2S2O3, 25 °C, 30 min, 76 %, 1.5:1 mixture of diastereomers; iv. CSA, (5.0 equiv), – 78→25 °C, 10 min, 72 % 1.5:1 mixture of diastereomers; v. Davis oxaziridine (2.0 equiv), THF, 0 °C, 2 h, 85 %, 1.5:1 mixture of diastereomers.