Synthesis of 10b-fluorinated analogues of protubonine a and its 11a-epimer via fluorocyclisation of tryptophan-containing dipeptides

Tomoya Fujiwara; Hiroko Yasuda; Yushi Nishimura; Hisanori Nambu; Takayuki Yakura

doi:10.1039/c4ra08741k

Synthesis of 10b-fluorinated analogues of protubonine a and its 11a-epimer via fluorocyclisation of tryptophan-containing dipeptides

Tomoya Fujiwara^*, Hiroko Yasuda, Yushi Nishimura, Hisanori Nambu, Takayuki Yakura

^*この論文の責任著者

分子合成化学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

5 被引用数 (Scopus)

抄録

The synthesis of 10b-fluorinated analogues of protubonine A and its 11a-epimer was accomplished using fluorocyclisation of tryptophan-containing dipeptides with N-fluoro-2,4,6-trimethylpyridinium triflate to 3a-fluoropyrrolo[2,3-b]indoles as a key step. Acetylation of the indole nitrogen and the following diketopiperazine formation gave the 10b-fluorinated analogues of protubonine A and its 11a-epimer.

本文言語	英語
ページ（範囲）	5464-5473
ページ数	10
ジャーナル	RSC Advances
巻	5
号	7
DOI	https://doi.org/10.1039/c4ra08741k
出版ステータス	出版済み - 2015

ASJC Scopus 主題領域

化学一般
化学工学一般

文献へのアクセス

10.1039/c4ra08741k

フィンガープリント

「Synthesis of 10b-fluorinated analogues of protubonine a and its 11a-epimer via fluorocyclisation of tryptophan-containing dipeptides」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル

@article{ee09884fa53c410284edd026b0890762,

title = "Synthesis of 10b-fluorinated analogues of protubonine a and its 11a-epimer via fluorocyclisation of tryptophan-containing dipeptides",

abstract = "The synthesis of 10b-fluorinated analogues of protubonine A and its 11a-epimer was accomplished using fluorocyclisation of tryptophan-containing dipeptides with N-fluoro-2,4,6-trimethylpyridinium triflate to 3a-fluoropyrrolo[2,3-b]indoles as a key step. Acetylation of the indole nitrogen and the following diketopiperazine formation gave the 10b-fluorinated analogues of protubonine A and its 11a-epimer.",

author = "Tomoya Fujiwara and Hiroko Yasuda and Yushi Nishimura and Hisanori Nambu and Takayuki Yakura",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2015.",

year = "2015",

doi = "10.1039/c4ra08741k",

language = "英語",

volume = "5",

pages = "5464--5473",

journal = "RSC Advances",

issn = "2046-2069",

publisher = "Royal Society of Chemistry",

number = "7",

}

TY - JOUR

T1 - Synthesis of 10b-fluorinated analogues of protubonine a and its 11a-epimer via fluorocyclisation of tryptophan-containing dipeptides

AU - Fujiwara, Tomoya

AU - Yasuda, Hiroko

AU - Nishimura, Yushi

AU - Nambu, Hisanori

AU - Yakura, Takayuki

PY - 2015

Y1 - 2015

N2 - The synthesis of 10b-fluorinated analogues of protubonine A and its 11a-epimer was accomplished using fluorocyclisation of tryptophan-containing dipeptides with N-fluoro-2,4,6-trimethylpyridinium triflate to 3a-fluoropyrrolo[2,3-b]indoles as a key step. Acetylation of the indole nitrogen and the following diketopiperazine formation gave the 10b-fluorinated analogues of protubonine A and its 11a-epimer.

AB - The synthesis of 10b-fluorinated analogues of protubonine A and its 11a-epimer was accomplished using fluorocyclisation of tryptophan-containing dipeptides with N-fluoro-2,4,6-trimethylpyridinium triflate to 3a-fluoropyrrolo[2,3-b]indoles as a key step. Acetylation of the indole nitrogen and the following diketopiperazine formation gave the 10b-fluorinated analogues of protubonine A and its 11a-epimer.

UR - http://www.scopus.com/inward/record.url?scp=84919776068&partnerID=8YFLogxK

U2 - 10.1039/c4ra08741k

DO - 10.1039/c4ra08741k

M3 - 学術論文

AN - SCOPUS:84919776068

SN - 2046-2069

VL - 5

SP - 5464

EP - 5473

JO - RSC Advances

JF - RSC Advances

IS - 7

ER -