Gallium(III)‐Catalyzed Cycloisomerization Approach to the Diterpenoid Alkaloids: Construction of the Core Structure for the Hetidines and Hetisines | Zendy

Hamlin Amy M. | Zendy; de Jesus Cortez Felipe | Zendy; Lapointe David | Zendy; Sarpong Richmond | Zendy

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Gallium(III)‐Catalyzed Cycloisomerization Approach to the Diterpenoid Alkaloids: Construction of the Core Structure for the Hetidines and Hetisines

Author(s) -

Hamlin Amy M.,

de Jesus Cortez Felipe,

Lapointe David,

Sarpong Richmond

Publication year - 2013

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201209030

Subject(s) - cycloisomerization , stereocenter , stereochemistry , terpenoid , chemistry , indene , aldol reaction , core (optical fiber) , gallium , catalysis , organic chemistry , enantioselective synthesis , materials science , composite material

A versatile core structure has been prepared that should provide a foundation for the syntheses of the hetidine‐ and hetisine‐type diterpenoid alkaloids. The synthesis of the caged polycyclic core structure, which features nine contiguous stereocenters, utilizes a Ga III ‐catalyzed cycloisomerization of an alkynyl indene as well as a Michael/aldol sequence to build the bicyclo[2.2.2] framework.

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