TY - JOUR
T1 - Protecting-Group-Free Formal Synthesis of Aspidospermidine
T2 - Ring-Opening Cyclization of Spirocyclopropane with Amine Followed by Regioselective Alkylations
AU - Nambu, Hisanori
AU - Tamura, Takafumi
AU - Yakura, Takayuki
N1 - Publisher Copyright:
Copyright © 2019 American Chemical Society.
PY - 2019/12/20
Y1 - 2019/12/20
N2 - A concise formal synthesis of (±)-aspidospermidine via Stork's intermediate, which could be used as a divergent synthesis of Aspidosperma alkaloids, was achieved by employing a ring-opening cyclization of spirocyclopropane with amine followed by a regioselective intramolecular/intermolecular alkylation sequence. Stork's intermediate was synthesized in only six steps from a simple starting material, 1,3-cyclohexanedione, and was converted into (±)-aspidospermidine. To the best of our knowledge, this synthesis of Stork's intermediate involves the least number of steps to date. Furthermore, no protecting groups were used during this synthesis.
AB - A concise formal synthesis of (±)-aspidospermidine via Stork's intermediate, which could be used as a divergent synthesis of Aspidosperma alkaloids, was achieved by employing a ring-opening cyclization of spirocyclopropane with amine followed by a regioselective intramolecular/intermolecular alkylation sequence. Stork's intermediate was synthesized in only six steps from a simple starting material, 1,3-cyclohexanedione, and was converted into (±)-aspidospermidine. To the best of our knowledge, this synthesis of Stork's intermediate involves the least number of steps to date. Furthermore, no protecting groups were used during this synthesis.
UR - http://www.scopus.com/inward/record.url?scp=85076240948&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.9b02469
DO - 10.1021/acs.joc.9b02469
M3 - 学術論文
C2 - 31746202
AN - SCOPUS:85076240948
SN - 0022-3263
VL - 84
SP - 15990
EP - 15996
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 24
ER -