TY - JOUR
T1 - Toward the Synthesis of Paspaline-Type Indole-Terpenes
T2 - Stereoselective Construction of Core Scaffold with Contiguous Asymmetric Quaternary Carbon Centers
AU - Hayakawa, Ichiro
AU - Matsumaru, Naochika
AU - Sakakura, Akira
N1 - Funding Information:
This work was supported by Grant-in-Aid for Scientific Research (grant number 20H02867) from the Japanese Society for the Promotion of Science (JSPS)/the Ministry of Education, Culture, Sports, Science, and Technology (MEXT), Japan, by a grant from the Sumitomo foundation, and by a grant from the Naito foundation. The authors thank the Division of Instrumental Analysis, Okayama University, for the NMR and HR-ESIMS measurements. We also thank Professor Koichi Mitsudo (Okayama University) for the X-ray crystallographic analysis.
Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/7/16
Y1 - 2021/7/16
N2 - The core scaffold of paspaline-type indole-terpenes was synthesized by using the House-Meinwald rearrangement as a key step. Rearrangement of the epoxide methyl group in the precursor with methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) as a Lewis acid proceeded smoothly to construct contiguous asymmetric quaternary carbon centers by a 1,2-chirality transfer.
AB - The core scaffold of paspaline-type indole-terpenes was synthesized by using the House-Meinwald rearrangement as a key step. Rearrangement of the epoxide methyl group in the precursor with methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) as a Lewis acid proceeded smoothly to construct contiguous asymmetric quaternary carbon centers by a 1,2-chirality transfer.
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U2 - 10.1021/acs.joc.1c01193
DO - 10.1021/acs.joc.1c01193
M3 - Article
AN - SCOPUS:85110962169
VL - 86
SP - 9802
EP - 9810
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 14
ER -