Literature DB >> 16378370

Phytochemical studies on Stemona plants: isolation of stemofoline alkaloids.

Thanapat Sastraruji1, Araya Jatisatienr, Stephen G Pyne, Alison T Ung, Wilford Lie, Morwenna C Williams.   

Abstract

Six new stemofoline alkaloids, (2'R)-hydroxystemofoline (5), (3'R)-stemofolenol (6), (3'S)-stemofolenol (7), 1',2'-didehydrostemofoline-N-oxide (8), the first C(19) stemofoline alkaloid, methylstemofoline (9), and the first glycosidated Stemona alkaloid, stemofolinoside (10), and three known alkaloids, (2'S)-hydroxystemofoline (2), (11Z)-1',2'-didehydrostemofoline (3), and (11E)-1',2'-didehydrostemofoline (4), have been isolated from a root extract of an unidentified Stemona species. The structure and relative configuration of these new alkaloids have been determined by spectral data interpretation and from semisynthetic studies.

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Year:  2005        PMID: 16378370     DOI: 10.1021/np050361y

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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