6- endo,6- endo,6- exo Cascade cyclization starting from vinyl radical; construction of a dodecahydrophenanthrene system

Treatment of 1-iodo-1,5-diene 3 with Bu 3SnH at 80°C afforded the 6- endo cyclized product 6. The reaction was extended further to achieve the transformation of 1-iodo-1,5,9,14-tetraene 10 into dodecahydrophenanthrene 11 under one electron reductive conditions via 6- endo,6- endo,6- exo cascade cycl...

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Bibliographic Details
Published in:Tetrahedron letters 1999-08, Vol.40 (34), p.6277-6280
Main Authors: Takasu, Kiyosei, Kuroyanagi, Jun-ichi, Katsumata, Akira, Ihara, Masataka
Format: Article
Language:English
Subjects:
alkenyl halides
cyclization
radical reactions
radicals
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Summary:Treatment of 1-iodo-1,5-diene 3 with Bu 3SnH at 80°C afforded the 6- endo cyclized product 6. The reaction was extended further to achieve the transformation of 1-iodo-1,5,9,14-tetraene 10 into dodecahydrophenanthrene 11 under one electron reductive conditions via 6- endo,6- endo,6- exo cascade cyclization. Free radical reaction of polyoleinic vinyl iodide at high temperature afforded phenanthrene derivative via 6- endo,6- endo,6- exo cascade cyclization, while mono-cyclized product through 5- exo mode was obtained at low temperature.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01234-4