954148-47-1Relevant academic research and scientific papers
Preparation of novel polycyclic heterocycles using a tin(II) chloride dihydrate-mediated deacetalisation-bicyclisation sequence
Cayley, Alex N.,Gallagher, Katherine A.,Menard-Moyon, Cecilia,Schmidt, Jan Peter,Diorazio, Louis J.,Taylor, Richard J. K.
body text, p. 3846 - 3856 (2009/07/04)
Tin(II) chloride dehydrate-mediated deacetalisation-bicyclisation procedures for the construction of novel polycyclic heterocycles from amides possessing a pendant acetal group are reported. Optimisation and scoping studies are described; using this metho
The first synthesis of the ABC-ring system of 'upenamide
Schmidt, Jan Peter,Beltran-Rodil, Sandra,Cox, Rhona J.,McAllister, Graeme D.,Reid, Mark,Taylor, Richard J. K.
, p. 4041 - 4044 (2008/02/11)
The first synthetic route to the spirooxaquinolizidinone core (ABC core) of the macrocyclic marine alkaloid 'upenamide (1) has been developed. All five stereocenters were introduced with complete stereocontrol. The hydroxyl group at C-11 was introduced by a regio- and stereoselective SeO2-mediated allylic oxidation. The spirocyclic skeleton was formed by a stannous chloride induced deacetalization-bicyclization procedure. Further stereocenters were introduced by an enzymatic desymmetrization and by incorporation of an (S)-malic acid derived building block.
