Literature DB >> 15497953

Phytochemical studies on Stemona burkillii prain: two new dihydrostemofoline alkaloids.

Pitchaya Mungkornasawakul1, Stephen G Pyne, Araya Jatisatienr, Wilford Lie, Alison T Ung, Kritchaya Issakul, Auntika Sawatwanich, Damrat Supyen, Chaiwat Jatisatienr.   

Abstract

Two new dihydrostemofoline alkaloids, 11(S),12(R)-dihydrostemofoline (3) and stemoburkilline (4), along with stemofoline (1) and 2'-hydroxystemofoline (2) have been isolated from a root extract of Stemona burkillii Prain. The structure and relative configuration of 3 have been determined via spectroscopic data and from comparison with synthetic 11(S),12(S)-dihydrostemofoline (5). The configuration of the exo-cyclic alkene group in 4 is tentively assigned as E on the basis of mechanistic considerations.

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Year:  2004        PMID： 15497953     DOI： 10.1021/np049791z

Source DB:  PubMed          Journal:  J Nat Prod        ISSN： 0163-3864            Impact factor:   4.050


  3 in total

1.  Asymmetric Formal Total Synthesis of the Stemofoline Alkaloids: The Evolution, Development and Application of a Catalytic Dipolar Cycloaddition Cascade.

Authors:  Charles S Shanahan; Chao Fang; Daniel H Paull; Stephen F Martin
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

2.  Application of an intramolecular dipolar cycloaddition to an asymmetric synthesis of the fully oxygenated tricyclic core of the stemofoline alkaloids.

Authors:  Ryan J Carra; Matthew T Epperson; David Y Gin
Journal:  Tetrahedron       Date:  2008-04-21       Impact factor: 2.457

3.  Enantioselective formal total syntheses of didehydrostemofoline and isodidehydrostemofoline through a catalytic dipolar cycloaddition cascade.

Authors:  Chao Fang; Charles S Shanahan; Daniel H Paull; Stephen F Martin
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-17       Impact factor: 15.336
  3 in total

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