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

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Citation

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.


Cite as: https://hdl.handle.net/11858/00-001M-0000-002C-0714-8
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.