501085-24-1Relevant articles and documents
Application of the chiral base desymmetrisation of imides to the synthesis of the alkaloid jamtine and the antidepressant paroxetine
Gill, Christopher D.,Greenhalgh, Daniel A.,Simpkins, Nigel S.
, p. 9213 - 9230 (2007/10/03)
The synthesis of the alkaloid jamtine and the antidepressant paroxetine have been addressed by a strategy involving asymmetric desymmetrisation of prochiral imides by a chiral lithium amide base. A short reaction sequence, starting with a cyclohexane fused succinimide, led to the structures originally reported for the alkaloid jamtine and its derived N-oxide. The structures synthesised are shown not to correspond with those originally reported. A second sequence involves desymmetrisation of a 4-arylglutarimide, and provides a short enantioselective synthesis of the drug substance paroxetine.
Asymmetric total synthesis of the proposed structure of the medicinal alkaloid jamtine using the chiral base approach.
Simpkins, Nigel S,Gill, Christopher D
, p. 535 - 537 (2007/10/03)
[reaction: see text] A highly step-economic asymmetric synthesis of the tetracyclic structure assigned to the medicinal alkaloid jamtine has been accomplished using a chiral lithium amide base desymmetrization of a ring-fused imide. The structure synthesi
