TY - JOUR
T1 - Synthesis of leuconoxine, leuconodine B, and rhazinilam by transformation of melodinine E via 6-hydro-21-dehydroxyleuconolam
AU - Umehara, Atsushi
AU - Ueda, Hirofumi
AU - Tokuyama, Hidetoshi
N1 - Funding Information:
This work was supported by the Drug Discovery and Life Science Research (BINDS) from AMED under Grant Number JP19am0101100 and JSPS KAKENHI Grant Numbers JP18H04379 in Middle Molecular Strategy, JP18H04231 in Precisely Designed Catalysts with Customized Scaffolding, and a Grant-in aid for Scientific Research (B) (18H02549) and (C) (17K08204).
Publisher Copyright:
© 2020 Elsevier Ltd
PY - 2021/1/22
Y1 - 2021/1/22
N2 - Synthesis of monoterpene indole alkaloids, leuconoxine, leuconodine B, and rhazinilam, by transformation of melodinine E via 6-hydro-21-dehydroxyleuconolam was established. The pivotal intermediate, 6-hydro-21-dehydroxyleuconolam, was prepared from melodinine E via a ring-opening N,S-acetal formation of the diaza[5.5.6.6]fenestrane skeleton and subsequent chemoselective reduction. These results demonstrate that 6-hydro-21-dehydroxy-leuconolam is a useful synthetic precursor of these related monoterpene indole alkaloids.
AB - Synthesis of monoterpene indole alkaloids, leuconoxine, leuconodine B, and rhazinilam, by transformation of melodinine E via 6-hydro-21-dehydroxyleuconolam was established. The pivotal intermediate, 6-hydro-21-dehydroxyleuconolam, was prepared from melodinine E via a ring-opening N,S-acetal formation of the diaza[5.5.6.6]fenestrane skeleton and subsequent chemoselective reduction. These results demonstrate that 6-hydro-21-dehydroxy-leuconolam is a useful synthetic precursor of these related monoterpene indole alkaloids.
KW - Aminal
KW - Biomimetic synthesis
KW - Divergent synthesis
KW - Monoterpene indole alkaloid
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U2 - 10.1016/j.tet.2020.131809
DO - 10.1016/j.tet.2020.131809
M3 - Article
AN - SCOPUS:85097753189
SN - 0040-4020
VL - 79
JO - Tetrahedron
JF - Tetrahedron
M1 - 131809
ER -