Synthesis of leuconoxine, leuconodine B, and rhazinilam by transformation of melodinine E via 6-hydro-21-dehydroxyleuconolam

Atsushi Umehara; Hirofumi Ueda; Hidetoshi Tokuyama

doi:10.1016/j.tet.2020.131809

Synthesis of leuconoxine, leuconodine B, and rhazinilam by transformation of melodinine E via 6-hydro-21-dehydroxyleuconolam

Atsushi Umehara, Hirofumi Ueda, Hidetoshi Tokuyama

研究成果: Article › 査読

1 被引用数 (Scopus)

抄録

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.

本文言語	English
論文番号	131809
ジャーナル	Tetrahedron
巻	79
DOI	https://doi.org/10.1016/j.tet.2020.131809
出版ステータス	Published - 2021 1月 22

ASJC Scopus subject areas

生化学
創薬
有機化学

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10.1016/j.tet.2020.131809

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title = "Synthesis of leuconoxine, leuconodine B, and rhazinilam by transformation of melodinine E via 6-hydro-21-dehydroxyleuconolam",

abstract = "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.",

keywords = "Aminal, Biomimetic synthesis, Divergent synthesis, Monoterpene indole alkaloid",

author = "Atsushi Umehara and Hirofumi Ueda and Hidetoshi Tokuyama",

note = "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: {\textcopyright} 2020 Elsevier Ltd",

year = "2021",

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doi = "10.1016/j.tet.2020.131809",

language = "English",

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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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