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Synthesis of the 1S,5R,9R- and 1S,5R,9S-C9-hydroxymethyl-5-phenylmorphan diastereomers 15 and 16. Reagents and conditions: (a) i. 3 N aq. HCl, THF, 16 h, ii. NaBH4, MeOH, 16 h, 69%, 1:1.5 13 (9R):14(9S); (b) BBr3, DCM, −78 °C→rt, 18 h, 13 to 15:81%, 14 to 16: 70%.
