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  One-step enantioselective synthesis of (4S)-isosclerone through biotranformation of juglone by an endophytic fungus

Prado, S., Buisson, D., Ndoye, I., Vallet, M., & Nay, B. (2013). One-step enantioselective synthesis of (4S)-isosclerone through biotranformation of juglone by an endophytic fungus. Tetrahedron Letters, 1189-1191. doi:10.1016/j.tetlet.2012.12.038.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-002C-0714-8 Version Permalink: https://hdl.handle.net/21.11116/0000-0009-3BBB-3
Genre: Journal Article

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EXT471.pdf (Publisher version), 446KB
 
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 Creators:
Prado, Soizic, Author
Buisson, Didier, Author
Ndoye, Idrissa, Author
Vallet, Marine1, Author           
Nay, Bastien, Author
Affiliations:
1External Organizations, ou_persistent22              

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 Abstract: We describe here a direct access to (4S)-isosclerone (+)-1, an important structural component of several
natural products featuring a spirobisnaphthalene ring system. Starting with the commercially available
5-hydroxy-1,4-naphthalenedione (juglone), biotransformation by the isosclerone-producing endophytic
fungus Paraconiothyrium variabile is described. The absolute configuration of (+)-1 was determined
unambiguously using circular dichroism and by measurement of the optical rotation. Moreover, the biotransformations
of other naphthalene derivatives were undertaken and led to the corresponding (4S)-
hydroxy-1-tetralone. At last, this work brings some insights on the biosynthesis of natural tetralones.

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 Dates: 2012-12-072012-12-242013
 Publication Status: Issued
 Pages: -
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 Rev. Type: -
 Identifiers: Other: EXT471
DOI: 10.1016/j.tetlet.2012.12.038
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Title: Tetrahedron Letters
  Other : Tetrahedron Lett.
Source Genre: Journal
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Publ. Info: Oxford : Pergamon
Pages: - Volume / Issue: - Sequence Number: - Start / End Page: 1189 - 1191 Identifier: ISSN: 0040-4039
CoNE: https://pure.mpg.de/cone/journals/resource/954925448772