NDLI: Aldol Condensations on a 3-Alkylidene-2,5-diketopiperazine: Synthesis of Two Marine Natural Products

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Aldol Condensations on a 3-Alkylidene-2,5-diketopiperazine: Synthesis of Two Marine Natural Products

Content Provider	Scilit
Author	Fairhurst, Magnus E. Zeeshan, Muhammad Haug, Bengt Erik Bayer, Annette
Copyright Year	2018
Description	Published as part of the Special Section $9^{th}$ EuCheMS Organic Division Young Investigator Workshop This work is dedicated to Prof. Leiv K. Sydnes on the occasion of his 70th birthday. The synthesis of two marine natural products containing a 3-alkylidene-6-arylidene-2,5-diketopiperazine scaffold by employing two consecutive aldol condensations starting with 1,4-diacetyl-2,5-diketopiperazine is reported. The target compounds contain a phenol or an imidazole group as aryl substituents, respectively, and suitable conditions for the aldol condensation of 1-acyl-3-alkylidene-2,5-diketopiperazine with the required functionalised aromatic aldehydes were developed. Provided the optimal base was used, introduction of the phenol group did not require use of a protecting group. Boc-protection was beneficial for introduction of the imidazole group, and conditions for carrying out the aldol condensation and Boc-deprotection in one step were identified. The stereochemistry of the target compounds was confirmed by NMR analysis.
Related Links	http://pdfs.semanticscholar.org/3879/49862d4d10ad57a3ae36a018ab5ef82b9e84.pdf http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0036-1591755.pdf
Ending Page	1306
Page Count	4
Starting Page	1303
ISSN	09365214
e-ISSN	14372096
DOI	10.1055/s-0036-1591755
Journal	Synlett
Issue Number	10
Volume Number	29
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2018-01-30
Access Restriction	Open
Subject Keyword	Organic Chemistry 5-diketopiperazine aldol Condensation
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry

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