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

TETRAHEDRON

卷:79

Article

Umehara, Atsushi¹  Ueda, Hirofumi¹  Tokuyama, Hidetoshi¹ 

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, 6-3 Aoba, Sendai, Miyagi 9808578, Japan

关键词: Monoterpene indole alkaloid;    Biomimetic synthesis;    Divergent synthesis;    Aminal;   

DOI  :  10.1016/j.tet.2020.131809

来源: Elsevier

【 摘 要 】

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. (C) 2020 Elsevier Ltd. All rights reserved.

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