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

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

Open Access

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

Author(s) -

Tomoya Fujiwara,

Hiroko Yasuda,

Yushi Nishimura,

Hisanori Nambu,

Takayuki Yakura

Publication year - 2014

Publication title -

rsc advances

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.746

H-Index - 148

ISSN - 2046-2069

DOI - 10.1039/c4ra08741k

Subject(s) - epimer , tryptophan , chemistry , stereochemistry , combinatorial chemistry , computational chemistry , amino acid , biochemistry

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.

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