TY - JOUR
T1 - Toward the Synthesis of SB-203207
T2 - Construction of Four Contiguous Nitrogen-Containing Stereogenic Centers
AU - Hayakawa, Ichiro
AU - Nagayasu, Anna
AU - Sakakura, Akira
N1 - Funding Information:
This work was supported by Grant-in-Aid for Scientific Research (Grant Number 25350960) 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 Kurata Grant awarded by the Kurata Memorial Hitachi Science and Technology; by a grant from the NOVARTIS Foundation (Japan) for the Promotion of Science; and by a grant from Wesco Scientific Promotion Foundation. The authors thank the Division of Instrumental Analysis, Okayama University, for the NMR and HR-ESIMS measurements. We would like to thank Professors Yoshiharu Iwabuchi and Yusuke Sasano (Tohoku University) for their gift of AZADO + ·BF 4 – and valuable discussions.
Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/12/6
Y1 - 2019/12/6
N2 - SB-203207 is an altemicidin-type alkaloid that potently inhibits isoleucyl tRNA synthetase activity. Its main structural feature is a hexahydro-6-azaindene framework containing a unique β-hydroxy α,α-disubstituted α-amino acid moiety on the cyclopentane portion. Herein we have established a method for constructing the four contiguous nitrogen-containing stereogenic centers of SB-203207 by using as key steps the stereoselective alkylation of bowl-shaped tricyclic lactone to construct a quaternary carbon at C1, the stereoselective hydroboration-oxidation reaction to install the C2 hydroxy group, and the Curtius rearrangement to introduce a nitrogen atom onto the C1 quaternary carbon.
AB - SB-203207 is an altemicidin-type alkaloid that potently inhibits isoleucyl tRNA synthetase activity. Its main structural feature is a hexahydro-6-azaindene framework containing a unique β-hydroxy α,α-disubstituted α-amino acid moiety on the cyclopentane portion. Herein we have established a method for constructing the four contiguous nitrogen-containing stereogenic centers of SB-203207 by using as key steps the stereoselective alkylation of bowl-shaped tricyclic lactone to construct a quaternary carbon at C1, the stereoselective hydroboration-oxidation reaction to install the C2 hydroxy group, and the Curtius rearrangement to introduce a nitrogen atom onto the C1 quaternary carbon.
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U2 - 10.1021/acs.joc.9b02627
DO - 10.1021/acs.joc.9b02627
M3 - Article
C2 - 31702152
AN - SCOPUS:85075428095
VL - 84
SP - 15614
EP - 15623
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 23
ER -