Abstract
A concise synthesis of (+)-pancratistatin and (+)-7-deoxypancratistatin from benzene using an enantioselective, dearomative carboamination strategy has been achieved. This approach, in combination with the judicious choice of subsequent olefin-type difunctionalization reactions, permits rapid and controlled access to a hexasubstituted core. Finally, minimal use of intermediary steps as well as direct, late stage C-7 hydroxylation provides both natural products in six and seven operations.
Publication types
-
Research Support, N.I.H., Extramural
-
Research Support, Non-U.S. Gov't
-
Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
-
Amaryllidaceae Alkaloids / chemical synthesis*
-
Amaryllidaceae Alkaloids / chemistry
-
Antineoplastic Agents / chemical synthesis*
-
Antineoplastic Agents / chemistry
-
Benzene / chemical synthesis
-
Benzene / chemistry*
-
Biological Products / chemical synthesis
-
Biological Products / chemistry
-
Catalysis
-
Chemistry Techniques, Synthetic / methods
-
Hydroxylation
-
Isoquinolines / chemical synthesis*
-
Isoquinolines / chemistry
-
Stereoisomerism
Substances
-
7-deoxypancratistatin
-
Amaryllidaceae Alkaloids
-
Antineoplastic Agents
-
Biological Products
-
Isoquinolines
-
pancratistatin
-
Benzene