A new synthetic route to tropane alkaloids. Pseudotropine and tropacocaine
β Scribed by Hideo Iida; Yohya Watanabe; Chihiro Kibayashi
- Book ID
- 104242319
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 227 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
β¦ Synopsis
Pseudotropine and tropacocaine have been synthesized by a facile route involving the [4 + 21 nitroso cycloaddition followed by interna1 Sn2 displacement. The tropane class of alkaloids have continued to elicit the unabated interests among organic chemists because of their pharmacological significance, and a great deal of work has been done on the stereochemical and synthetic problems.
1 Since a superb approach to tropinone (1) was devised by Robinson, 2
a number of syntheses of some tropanes have been reported.
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## Abstract Starting from ethyl 2βcyclohexenβ1βcarboxylate (**3**) the total synthesis of the perhydrohistrionicotoxin intermediate **23** was achieved in 25% overallβyield. The two key steps involve a positionally specific addition of HOBr to the oximeβolefin **7** and the alkylation of bromooxime
## Abstract For Abstract see ChemInform Abstract in Full Text.
A. I. tiit;iigorodsky. M o l i , i iihr C'rrsrd\ a t i d .Wolaii/i~s. Academic Press. New Yoi-k. 1973. Chapter IA.6. [i] I n ii wider sense, all noncentrosymmetric crystal structures are polar: in a more restricted sense, this applies only to those permitting a permanent dipole moiiiciit. The latter