After reluctantly giving the three young scientists top-level security clearance and field authorization, M turned to give them his parting words of wisdom.

"Blofeld is very dangerous and conniving! Despite having already stolen all of the nakiterpiosin synthesized by scientists around the world, he wants more of it! We don't know what his nefarious plans he has for the compound, but we have received information that he is currently attempting to make more of it. Your mission is to discover his intent, recover the stolen compound, and stop him from synthesizing any more of it. We know that he has already made large steps towards the successful synthesis. Here is the experimental of the step is currently attempting. Good luck!"

Picking up his trusty crate of supplies and his spare pair of glasses, M hurried away to his office, leaving the three newly-minted agents with the experimental in their hands and a mild sinking feeling in their stomachs.

56. To a previously obtained solution of 55, borontrifluoride diethyl etherate and triethylsilane in methylene chloride were slowly added at 0 °C. After stirring at same temperature for 2 hours, a saturated aqueous solution of sodium bicarbonate was added. The biphasic mixture was extracted with ethyl acetate, and the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (20% ethyl acetate–hexanes). 1H NMR: δ 7.90 (d, 1H, J=8.0 Hz), 7.34 (d, 1H, J=8.0 Hz), 6.32 (d, 1H, J=10.0 Hz), 5.29 (s, 1H), 4.71 (dd, 1H, J=3.5 Hz, 2.5 Hz), 4.41 (dd, 1H, J=7.9 Hz, 3.2Hz), 4.25 (dd, 1H, J=7.8 Hz), 4.10 (d, 1H, J=11.0 Hz), 3.93 (ddd, 1H, J=8.1 Hz, 7.9 Hz, 3.9 Hz), 3.89 (dd, 1H, J=10.0 Hz, 3.2 Hz), 3.55 (ddd, 1H, J=12.7 Hz, 9.4 Hz, 2.3 Hz), 3.12 (dd, 1H, J=11.0 Hz, 1.0 Hz), 2.75 (ddd, 1H, J=13.7 Hz, 2.5 Hz, 2.3 Hz), 2.72 (s, 3H), 2.73-2.69 (1H, m), 2.70 (d, 1H, J=9.4 Hz), 2.29 (ddd, 1H, J=13.7 Hz, 12.7 Hz, 3.4 Hz), 2.61 (dd, 1H, J=12.4 Hz, 7.87 Hz), 2.06 (dd, 1H, J=12.4 Hz, 1.0 Hz), 1.72 (ddd, 2H, J=13.2 Hz, 8.2 Hz, 8.1 Hz), 1.51 (s, 3H), 1.15 (d, 3H, J=7.3 Hz), 0.95 (s, 9H), 0.28 (s, 3H), 0.15 (s, 3H), 4.00-1.57(s, 1H).

Note: The experimental for this step was extrapolated from that for the synthesis of compound 10 from 29 on page 378 as the exact experimental for 55 to 56 was not given and the step of 29 to 10 uses the same reagents and reaction conditions.

Back | Next
Return to Main SSG Page