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Synfacts 2005(3): 0271-0271  
DOI: 10.1055/s-2005-921597
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Lucilactaene

Contributor(s): Philip Kocienski
J. Yamaguchi, H. Kakeya, T. Uno, M. Shoji, H. Osada, Y. Hayashi*
Tokyo University of Science, Japan
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

NG-391 is a neuronal cell protecting agent isolated from Fusarium sp. RK97-94. Lucilactaene was also isolated from the same organism and it arrests cell cycle progression in p53-transfected cancer cells. An asymmetric synthesis of NG-301 (Y. Hayashi, J. Yamaguchi, M. Shoji Tetrahedron 2002, 58, 9839-9846) established its absolute configuration whereas Lucilactaene isolated from the same culture broth was racemic. The authors surmised that the Lucilactaene is biogenetically derived from NG-391 and experiments showed that racemization occurred very easily during isolation.