Synthesis of musafluorone: a naphthoxanthenone isolated from Musa acuminata

Musafluorone was synthesized using a nine-step procedure including a Grignard addition and a photochemical cyclization. 5-Methoxy-3 H-naphtho[2,1,8- mna]xanthen-3-one (musafluorone, 1), the only naphthoxanthenone reported so far from Musaceae, was synthesized starting from 2-naphthol in nine steps a...

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Bibliographic Details
Published in:Tetrahedron letters 2010-09, Vol.51 (35), p.4640-4643
Main Authors: Duque, Luisa, Restrepo, Catalina, Sáez, Jairo, Gil, Jesús, Schneider, Bernd, Otálvaro, Felipe
Format: Article
Language:English
Subjects:
Grignard addition
Naphthoxanthenones
Phenylphenalenones
Photochemical cyclization
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Summary:Musafluorone was synthesized using a nine-step procedure including a Grignard addition and a photochemical cyclization. 5-Methoxy-3 H-naphtho[2,1,8- mna]xanthen-3-one (musafluorone, 1), the only naphthoxanthenone reported so far from Musaceae, was synthesized starting from 2-naphthol in nine steps and resulted in an overall yield of 3%. Grignard addition of phenylmagnesium bromide to 4-methoxyperinaphthenone afforded the corresponding 4-methoxy-9-phenylphenalenone which, after epoxidation and methyl transposition, was subjected to a photochemical cyclization procedure to furnish 1.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.06.128