TY - JOUR
T1 - Elucidation of Racemization Process of Azaspirene Skeleton in Neutral Aqueous Media
AU - Hirasawa, Shun
AU - Mukai, Ken
AU - Sakai, Shinnosuke
AU - Wakamori, Shinnosuke
AU - Hasegawa, Takahiro
AU - Souma, Kazunori
AU - Kanomata, Nobuhiro
AU - Ogawa, Narihito
AU - Aizawa, Mamoru
AU - Emoto, Makoto
N1 - Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/12/7
Y1 - 2018/12/7
N2 - Azaspirene and related congeners, which possess various biological activities, have a unique spirocyclic core structure. However, there are few studies on the chemical properties of (-)-azaspirene, despite the fact that it may provide important insights into unveiling the biosynthetic pathway. Here, we report a nine-step chemical synthesis of an azaspirene analogue with a new finding that the natural (-)-azaspirene skeleton easily racemizes in neutral aqueous media.
AB - Azaspirene and related congeners, which possess various biological activities, have a unique spirocyclic core structure. However, there are few studies on the chemical properties of (-)-azaspirene, despite the fact that it may provide important insights into unveiling the biosynthetic pathway. Here, we report a nine-step chemical synthesis of an azaspirene analogue with a new finding that the natural (-)-azaspirene skeleton easily racemizes in neutral aqueous media.
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U2 - 10.1021/acs.joc.8b02223
DO - 10.1021/acs.joc.8b02223
M3 - Article
C2 - 30381952
AN - SCOPUS:85058189205
SN - 0022-3263
VL - 83
SP - 14457
EP - 14464
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 23
ER -