AgNTf2-mediated allylation with allylsilanes at C3a-position of hexahydropyrroloindoles: Application to total syntheses of amauromine alkaloids

Hiroyuki Hakamata; Soichiro Sato; Hirofumi Ueda; Hidetoshi Tokuyama

doi:10.1021/acs.orglett.7b02602

AgNTf₂-mediated allylation with allylsilanes at C3a-position of hexahydropyrroloindoles: Application to total syntheses of amauromine alkaloids

Hiroyuki Hakamata, Soichiro Sato, Hirofumi Ueda, Hidetoshi Tokuyama

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

A protocol for the allylation at the C3a-position of hexahydropyrroloindole using allylsilanes is developed. AgNTf2 proved to be an efficient activator of halopyrroloindoline substrates. This method is applicable to the introduction of various allyl groups including the reverse prenyl group. The utility of this reaction is demonstrated by total synthesis of amauromine alkaloids. Stepwise bromocyclizations of the bis-indolylmethyl diketopiperazine derivative and subsequent double reverse prenylation furnished (+)-novoamauromine and (-)-epiamauromine.

Original language	English
Pages (from-to)	5308-5311
Number of pages	4
Journal	Organic letters
Volume	19
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.7b02602
Publication status	Published - 2017 Oct 6

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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@article{5cf125a1ffc94652b521568ac1f018a0,

title = "AgNTf2-mediated allylation with allylsilanes at C3a-position of hexahydropyrroloindoles: Application to total syntheses of amauromine alkaloids",

abstract = "A protocol for the allylation at the C3a-position of hexahydropyrroloindole using allylsilanes is developed. AgNTf2 proved to be an efficient activator of halopyrroloindoline substrates. This method is applicable to the introduction of various allyl groups including the reverse prenyl group. The utility of this reaction is demonstrated by total synthesis of amauromine alkaloids. Stepwise bromocyclizations of the bis-indolylmethyl diketopiperazine derivative and subsequent double reverse prenylation furnished (+)-novoamauromine and (-)-epiamauromine.",

author = "Hiroyuki Hakamata and Soichiro Sato and Hirofumi Ueda and Hidetoshi Tokuyama",

note = "Funding Information: This work was financially supported by JSPS KAKENHI Grant Numbers JP16H01127 in Middle Molecular Strategy and JP16H00999 in Precisely Designed Catalysts with Customized Scaffolding, a Grant-in aid for Scientific Research (A) (26253001) and (C) (17K08204), and the Platform Project for Supporting Drug Discovery and Life Science Research funded by Japan Agency for Medical Research and Development (AMED). Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = oct,

day = "6",

doi = "10.1021/acs.orglett.7b02602",

language = "English",

volume = "19",

pages = "5308--5311",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - AgNTf2-mediated allylation with allylsilanes at C3a-position of hexahydropyrroloindoles

T2 - Application to total syntheses of amauromine alkaloids

AU - Hakamata, Hiroyuki

AU - Sato, Soichiro

AU - Ueda, Hirofumi

AU - Tokuyama, Hidetoshi

N1 - Funding Information: This work was financially supported by JSPS KAKENHI Grant Numbers JP16H01127 in Middle Molecular Strategy and JP16H00999 in Precisely Designed Catalysts with Customized Scaffolding, a Grant-in aid for Scientific Research (A) (26253001) and (C) (17K08204), and the Platform Project for Supporting Drug Discovery and Life Science Research funded by Japan Agency for Medical Research and Development (AMED). Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/10/6

Y1 - 2017/10/6

N2 - A protocol for the allylation at the C3a-position of hexahydropyrroloindole using allylsilanes is developed. AgNTf2 proved to be an efficient activator of halopyrroloindoline substrates. This method is applicable to the introduction of various allyl groups including the reverse prenyl group. The utility of this reaction is demonstrated by total synthesis of amauromine alkaloids. Stepwise bromocyclizations of the bis-indolylmethyl diketopiperazine derivative and subsequent double reverse prenylation furnished (+)-novoamauromine and (-)-epiamauromine.

AB - A protocol for the allylation at the C3a-position of hexahydropyrroloindole using allylsilanes is developed. AgNTf2 proved to be an efficient activator of halopyrroloindoline substrates. This method is applicable to the introduction of various allyl groups including the reverse prenyl group. The utility of this reaction is demonstrated by total synthesis of amauromine alkaloids. Stepwise bromocyclizations of the bis-indolylmethyl diketopiperazine derivative and subsequent double reverse prenylation furnished (+)-novoamauromine and (-)-epiamauromine.

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