Synthesis of oxa[9]helicene derivatives by cyclodehydration of 1,1′-bibenzo[c]phenanthrene-2,2′-diol using phosphorus pentoxide

[Display omitted] •Synthesis of enantiomerically pure oxa[9]helicenes by cyclodehydration reaction.•P2O5 was optimal among several cyclodehydration reaction conditions.•Chiroptical properties of oxa[9]helicene were shown by ECD measurement.•Oxa[9]helicenes with several substituents were synthesized....

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Bibliographic Details
Published in:Tetrahedron letters 2021-04, Vol.69, p.152948, Article 152948
Main Authors: Hossain, Md. Sharif, Akter, Mahmuda, Karikomi, Michinori
Format: Article
Language:English
Subjects:
Cyclodehydration
Furan ring
Oxahelicene
Phosphorus pentoxide
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Summary:[Display omitted] •Synthesis of enantiomerically pure oxa[9]helicenes by cyclodehydration reaction.•P2O5 was optimal among several cyclodehydration reaction conditions.•Chiroptical properties of oxa[9]helicene were shown by ECD measurement.•Oxa[9]helicenes with several substituents were synthesized. A new one-step cyclization reaction has been established for the synthesis of oxa[9]helicene derivatives, containing eight ortho-condensed benzene rings and one furan ring. 1,1′-Bibenzo[c]phenanthrene-2,2′-diols (HEBPOLs) afforded the corresponding oxa[9]helicenes by refluxing with phosphorous pentoxide (P2O5) in o-dichlorobenzene. Enantiomerically pure oxa[9]helicenes were also synthesized with retention of the configuration and enantiopurity (>98% ee) from the corresponding enantiomerically pure HEBPOLs.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2021.152948