Towards total synthesis of communesins and Perophoramidine: Unexpected cascade reaction of Michael–Mannich–Mannich additions

Wu, Haoxing, Xiao, Xue and Qin, Yong (2011) Towards total synthesis of communesins and Perophoramidine: Unexpected cascade reaction of Michael–Mannich–Mannich additions. Synlett, 7: 907-910. doi:10.1055/s-0030-1259705

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Author Wu, Haoxing
Xiao, Xue
Qin, Yong
Title Towards total synthesis of communesins and Perophoramidine: Unexpected cascade reaction of Michael–Mannich–Mannich additions
Journal name Synlett   Check publisher's open access policy
ISSN 0936-5214
1437-2096
Publication date 2011-04
Sub-type Article (original research)
DOI 10.1055/s-0030-1259705
Issue 7
Start page 907
End page 910
Total pages 4
Place of publication Stuttgart, Germany
Publisher Georg Thieme
Collection year 2012
Language eng
Formatted abstract
A new type of chiral amidinobenzodiene 5 was prepared from isatin in ten steps. While attempting to prepare the core structure from 5 and tryptamine derivative 17 via a hetero Diels–Alder reaction for the total synthesis of communesin and perophoramidine,
we observed an unexpected three-step, one-pot cascade reaction of Michael–Manich–Manich additions. The cascade reaction between 5 and 17 yielded diasteromers 21a and 21b with a complex polycyclic skeleton of 2,3,4,5-diindolinohexahydropyrrole in 76%
yield and a ratio of 3:1. The stereochemistry of 21a was confirmed by X-ray crystal-structural analysis.
Keyword Communesin
Perophoramidine
Cascade reactions
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status Non-UQ
Additional Notes Received 12 October 2010

Document type: Journal Article
Sub-type: Article (original research)
Collections: Non HERDC
Institute for Molecular Bioscience - Publications
 
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Citation counts: TR Web of Science Citation Count  Cited 11 times in Thomson Reuters Web of Science Article | Citations
Scopus Citation Count Cited 10 times in Scopus Article | Citations
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Created: Mon, 04 Jun 2012, 14:35:33 EST by Sean Xiao on behalf of Institute for Molecular Bioscience