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Strychnos 1990 - 2004 - Crops for the Future

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Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bonjoch, J., J. Quirante, D. Sole, J. Castells, M. Galceran and J. Bosch<br />

Functionalized 2-azabicyclo(3.3.1)nonanes .14. 8-aryl-2-azabicyclo[3.3.1]nonan-7<br />

1991<br />

Tetrahedron<br />

47(25): 4417-4428<br />

Abstract<br />

The syn<strong>the</strong>sis of 8-aryl-2-azabicyclo[3.3.1]nonan-7-ones (7) by acid cyclization of 4-(3-aryl-2-<br />

oxopropyl)-2-piperidinecarbonitriles (5) is reported. Bicyclic alpha-aril-beta-amino ketones 7 easily<br />

undergo a retro-Michael ring opening to give <strong>the</strong> corresponding 2-arylcyclohexenones 8.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bosch, J., M. Salas, M. Amat, M. Alvarez, I. Morgo and B. Adrover<br />

Studies on <strong>the</strong> syn<strong>the</strong>sis of <strong>Strychnos</strong> indole alkaloids<br />

1991<br />

Tetrahedron<br />

47(28): 5269-5276<br />

Abstract<br />

Tetracycles 3b-d, having <strong>the</strong> ABCD ring substructure of <strong>Strychnos</strong> alkaloids and a N(b)-<br />

(<strong>for</strong>mylmethyl) substituent protected as an oxime or hydrazone derivative, have been prepared by<br />

nucleophilic addition of <strong>the</strong> enolate of indoleacetic ester 1 to pyridinium salts 2b-d followed by acid<br />

cyclization. The same one-pot, two-step sequence allowed <strong>the</strong> preparation of tetracycle 3f, which<br />

incorporates an alpha-methoxyacrylate chain at <strong>the</strong> piperidine beta-position.

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