Rearrangements of the 2,6-diaryl-3,7-dioxabicyclo[3.3.0] octane skeleton, Part III. Reaction of gmelinol with BF3-etherate and N,N-dimethylaniline

DOI: 10.1016/0040-4020(96)00887-3

Source and publish data:

Tetrahedron p. 14349 - 14360 (1996)

Update date:2022-08-29

Topics:

Authors:

Ward, Robert S.

Pelter, Andrew

Venkateswarlu, Revuru

Kamakshi, Chakicherla

Lakshmi, Ayalasomayajula

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Article abstract of DOI:10.1016/0040-4020(96)00887-3

Reaction of gmelinol 1 with BF₃-etherate and N,N-dimethylaniline gave a product 9 formed by rearrangement of the 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane skeleton. Compound 9 on reduction with BF₃-etherate and triethylsilane produced 15 which is epimeric with di-O-methyl cycloolivil 18.

Full text of DOI:10.1016/0040-4020(96)00887-3

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