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19 The direct hydroboration of alcohol (+)-2 without silylation of the homoallylic alcohol function (BH3 ·THF then H2 O2 , NaOH) led to the formation of 5 and 5 ′ with an overall yield of 50% and a 60/40 ratio of 5 /5 ′. See ref.
[18
20 Compound (+)-11 ′ was synthesized according to a strategy similar to the one used for obtaining (+)-11 However the deprotection of the PMP group by using CAN produced the decomposition of 11 ′.
Scheme 4
21 (-)-Slaframine was transformed into the more stable N -acetylslaframine (Ac2 O pyridine): [α]D
20 -13.3 (c 0.8, EtOH) {lit.
[16c D
20 -11.2 (c 1.45, EtOH)}; mp 138-140 °C (lit.
[16c 3 ): 3300, 1730, 1650, 1545, 1440 cm-1 ; 1 H NMR (CDCl3 , 300 MHz) δ = 6.62 (br m, 1 H), 5.25 (ddd, 1 H, J = 7.4, 4.8, 2.2 Hz), 4.21 (dt, 1 H J = 8.5, 2.9 Hz), 3.14-3.02 (m, 2 H), 2.29 (m, 1 H), 2.19 (dd, 1 H, J = 11.4, 2.6 Hz), 2.08 (s, 3 H), 2.00 (s, 3 H), 2.07-1.87 (m, 2 H), 1.81 (m, 1 H), 1.65-1.56 (m, 2 H), 1.48 (m, 1 H); 13 C NMR (CDCl3 , 75 MHz) δ = 170.5 (s), 169.3 (s), 74.4 (d), 67.4 (d), 57.4 (t), 52.9 (t), 43.6 (d), 30.3 (t), 28.0 (t), 23.2 (q), 21.0 (q), 20.3 (t). The physical and spectral data are identical to those reported.
[16c n
22 Groutas WC.
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