Abstract
| - (+)-Pyrido[3,4-b]homotropane (PHT) was efficiently constructed in 12 steps from N,N-diisopropylisonicotinamide. The synthesis features (i) RCM reaction in installing the homotropane skeleton, (ii) Snieckus ortho-lithiation of N,N-diisopropylisonicotinamide followed by acylation, (iii) Myer reduction of bulky tertiary amide to alcohol with LiBH3NH2, and (iv) utilization of l-glutamic acid to introduce and establish the requisite stereogenic centers.
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