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

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

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

5 Scopus citations

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.

Original language	English
Pages (from-to)	5464-5473
Number of pages	10
Journal	RSC Advances
Volume	5
Issue number	7
DOIs	https://doi.org/10.1039/c4ra08741k
State	Published - 2015

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering

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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",

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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 -

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

Abstract

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