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Synthesis of 5-endo-, 5-exo-, 6-endo- and 6-exo-hydroxylated analogues of epibatidine

✍ Scribed by Zhi-Liang Wei; Clifford George; Alan P. Kozikowski

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 171 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)00737-8

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✦ Synopsis

A convenient, high-yield synthesis of N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one (7) was developed by SmI 2 -mediated desulfonylation of 6. Thus, 5-endo-, 5-exo-, 6-endo-, and 6-exo-hydroxylated epibatidine analogues 2a,b and 3a,b were synthesized from 7 by using a Pd(PPh 3 ) 4 -catalyzed reductive Heck coupling reaction and SmI 2 -mediated reduction of the carbonyl group as the key steps. Other reaction conditions for the reductive Heck procedure and the reduction step were also investigated.

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