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1.
Chem Commun (Camb) ; 52(71): 10747-50, 2016 Sep 14.
Article in English | MEDLINE | ID: mdl-27507662

ABSTRACT

The synthesis of dehaloperophoramidine, a non-halogenated derivative of the marine natural product perophoramidine, and its biological activity towards HCT116, HT29 and LoVo colorectal carcinoma cells is reported. A [3,3]-Claisen rearrangement and an epoxide opening/allylsilylation reaction installed the contiguous all-carbon quaternary stereocentres with the required relative stereochemistry.

2.
Org Biomol Chem ; 8(2): 442-50, 2010 Jan 21.
Article in English | MEDLINE | ID: mdl-20066282

ABSTRACT

A study of the effect of substrate structure on a Claisen-aza-Cope reaction is presented including a rationalisation of the reaction outcome using DFT calculations. An asymmetric version of the reaction is also described that is of relevance to a proposed approach to the communesin family of natural products.


Subject(s)
Indoles/chemistry , Quinolines/chemistry , Biological Products/chemical synthesis , Quantum Theory , Thermodynamics
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