I15-Hydroxy-4-oxo-IO-pentadecynoic acid lactone (2i): oil; 'H NMR (CDCI,, 300 MHz, ppm) 1.38 (6 H, m), 1.50-1.77 (4 H, m, C6-H2 and C14-H2), 2.12 (4 H, m, C9-H2 and C12-H2), 2.43 (2 H, t, J = 6.0 Hz, C5-H,), 2.50 (2 H, t, J = 5.8 Hz, C2-H2 or C3-H,), 2.68 (2 H, t, J = 5.8 Hz, C3-H2 or C2cm-l; EIMS, m / e (relative intensity) 93 (44), 79 (94). 67 (39), 55 (base, C4H7+); ClMS (isobutane), m / e 251 (M' + H); EIHRMS, m / e 250.1567 (C,5H2203 requires 250.1569). (Z)-15-Hydroxy-4-oxo-8-pentadecenoic acid lactone (2j): oil; IH NMR (CDCI,, 300 MHz, ppm) 1.36 (6 H, m). 1.56-1.77 (4 H, m), 2.02 (4 H, m, C7-H2 and CIO-HI), 2.46 (2 H, t. J = 6.0 Hz, C5-H,), 2.59 (2 H, t, J = 5.9 Hz, C2-H2 or C3-H2), 2.75 (2 H, t, J = 5.9 Hz, C3-H2 or C2-H2), 4.15 (2 H, t, J = 5.3 Hz, C15-H2), 5.40 (2 H, m, CH=CH); IR (neat) Y

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The β-amino alcohol 4β-morpholinocaran-3α-ol is prepared by addition of morpholine to α-3,4-epoxycarane utilizing anhydrous magnesium bromide as Lewis acid promoter. The enantiopure amino alcohol is uniquely effective as a chiral moderator for the addition of lithium cyclopropylacetylide to an unprotected N-acylketimine. This reaction provides an efficient route to the second generation NNRTI drug candidate DPC 963.