TY - JOUR
T1 - Synthesis of (±)-aphanorphine
T2 - a new approach to tricyclic 3-benzazepine scaffold using two radical C-C bond-forming reactions
AU - Yoshimitsu, Takehiko
AU - Atsumi, Chie
AU - Iimori, Emiko
AU - Nagaoka, Hiroto
AU - Tanaka, Tetsuaki
N1 - Funding Information:
This work was supported by a Grant-in-Aid [KAKENHI KIBAN KENKYU (C) No. 19590006] from the Ministry of Education, Culture, Sports, Science and Technology, Japan.
PY - 2008/7/21
Y1 - 2008/7/21
N2 - An expeditious approach to (±)-aphanorphine has been established using readily available starting materials. The present synthesis relies on the direct assembly between N-methylpyrrolidone (NMP) and 2-bromoanisaldehyde, which takes place through Et3B/air-mediated transformation of the α-nitrogen-substituted sp3C-H bond, and features a new design concept for the synthesis of the tricyclic 3-benzazepine skeleton.
AB - An expeditious approach to (±)-aphanorphine has been established using readily available starting materials. The present synthesis relies on the direct assembly between N-methylpyrrolidone (NMP) and 2-bromoanisaldehyde, which takes place through Et3B/air-mediated transformation of the α-nitrogen-substituted sp3C-H bond, and features a new design concept for the synthesis of the tricyclic 3-benzazepine skeleton.
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U2 - 10.1016/j.tetlet.2008.05.058
DO - 10.1016/j.tetlet.2008.05.058
M3 - Article
AN - SCOPUS:44949109025
SN - 0040-4039
VL - 49
SP - 4473
EP - 4475
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 29-30
ER -