- Pictet-Spengler reaction: Is carbonyl the best choice? A highly diastereoselective alternative approach to trans-1,3-disubstituted tetrahydro-β-carbolines
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Unprecedented 1,2,3-trisubstituted tetrahydro-β-carbolines (THBCs) have been synthesized via a short and highly diastereoselective synthetic route. The key step of the sequence is a flexible variant of the Pictet-Spengler reaction employing synthetic equivalents of several non-available carbonyl compounds. Using one such synthon, the resultant THBC could be further ring- closed to a tetracyclic indole alkaloidal skeleton. (C) 2000 Elsevier Science Ltd.
- Singh, Kamaljit,Deb, Prasant K.
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- Modified Pictet-Spengler reaction. A highly diastereoselective approach to 1,2,3-trisubstituted-1,2,3,4-tetrahydro-β-carbolines using perhydro-1,3-heterocycles
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A flexible variant of the Pictet-Spengler reaction employing oxazinanes as synthetic equivalents of several carbonyl compounds has been developed. Using acid catalyzed one pot condensation of perhydro-1,3-heterocycles various 1,3-disubstituted and 1,2,3-trisubstituted-1,2,3,4-tetrahydro-β-carbolines (THBCs) have been synthesized diastereoselectively.
- Singh, Kamaljit,Deb, Prasant K,Venugopalan
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p. 7939 - 7949
(2007/10/03)
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