Details

Autor(en) / Beteiligte

• Takasu, Kiyosei
• Kuroyanagi, Jun-ichi
• Katsumata, Akira
• Ihara, Masataka

Titel

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

Ist Teil von

• Tetrahedron letters, 1999-08, Vol.40 (34), p.6277-6280

Ort / Verlag

Elsevier Ltd

Erscheinungsjahr

1999

Quelle

Elsevier Journal Backfiles on ScienceDirect (DFG Nationallizenzen)

Beschreibungen/Notizen

• 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.