Total synthesis of (-)-colchicine via a Rh-triggered cycloaddition cascade |
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Authors: | Graening Timm Bette Virginie Neudörfl Jörg Lex Johann Schmalz Hans-Günther |
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Affiliation: | Universit?t zu K?ln, Greinstrasse 4, D-50939 K?ln, Germany. |
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Abstract: | [reaction: see text] A synthesis of the antimitotic alkaloids (-)-colchicine and (-)-isocolchicine is reported. Important steps are (a) enantioselective transfer-hydrogenation of an alkynone, (b) iodine/magnesium exchange with subsequent aromatic acylation, (c) Rh-catalyzed transformation of an alpha-diazoketone into an oxatetracyclic key intermediate through intramolecular [3 + 2]-cycloaddition of an in situ generated carbonyl ylide, and (d) regioselective conversion of the cycloadduct into a tropolone derivative. The new synthetic strategy opens an efficient enantioselective access to colchicine and structural analogues. |
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