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Total synthesis of debromoflustramine B via biomimetic alkylative cyclization

Total synthesis of debromoflustramine B via biomimetic alkylative cyclization
Total synthesis of debromoflustramine B via biomimetic alkylative cyclization
The hexahydropyrrolo[2,3-b]indoline skeleton is readily accessed by the zinc triflate-mediated alkylation of tryptamine derivatives. The methodology was employed in a three-step total synthesis of debromoflustramine B.
bryozoan flustra-foliacea, marine alkaloids, cyclic tautomers, tryptophan, chemistry, (+)-ent-debromoflustramine-b, (+/-)-debromoflustramine-b, (-)-pseudophrynaminol, pyrroloindoles, pseudophrynaminol
1523-7060
1801-1803
Tan, Gan Hup
e297e62c-4b4d-4182-8a89-7b4af2585806
Zhu, Xiuwen
dbfbc3db-424b-4f1a-9865-3093a88a5c3c
Ganesan, A.
62aa5a87-9308-4383-8686-99726b6bcfb9
Tan, Gan Hup
e297e62c-4b4d-4182-8a89-7b4af2585806
Zhu, Xiuwen
dbfbc3db-424b-4f1a-9865-3093a88a5c3c
Ganesan, A.
62aa5a87-9308-4383-8686-99726b6bcfb9

Tan, Gan Hup, Zhu, Xiuwen and Ganesan, A. (2003) Total synthesis of debromoflustramine B via biomimetic alkylative cyclization. Organic Letters, 5 (10), 1801-1803. (doi:10.1021/ol034516+).

Record type: Article

Abstract

The hexahydropyrrolo[2,3-b]indoline skeleton is readily accessed by the zinc triflate-mediated alkylation of tryptamine derivatives. The methodology was employed in a three-step total synthesis of debromoflustramine B.

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More information

Published date: 15 May 2003
Keywords: bryozoan flustra-foliacea, marine alkaloids, cyclic tautomers, tryptophan, chemistry, (+)-ent-debromoflustramine-b, (+/-)-debromoflustramine-b, (-)-pseudophrynaminol, pyrroloindoles, pseudophrynaminol

Identifiers

Local EPrints ID: 20086
URI: http://eprints.soton.ac.uk/id/eprint/20086
ISSN: 1523-7060
PURE UUID: 7bcbdf18-d4f6-4c46-9795-b97738fa5cfe

Catalogue record

Date deposited: 24 Feb 2006
Last modified: 15 Mar 2024 06:21

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Contributors

Author: Gan Hup Tan
Author: Xiuwen Zhu
Author: A. Ganesan

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