RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2017; 49(22): 5003-5006
DOI: 10.1055/s-0036-1588477
DOI: 10.1055/s-0036-1588477
paper
Total Synthesis of Lagerstannin C: Follow-up of the Khanbabaee’s Synthesis
The Ministry of Education, Culture, Sports Science & Technology in Japan supported the program for the Strategic Research Foundation at Private Universities (S1311046), JSPS KAKENHI (Grant Number JP15K13650, JP16H01163 in Middle Molecular Strategy, and JP16KT0061) partly supported this work. We thank Osaka Synthetic Chemical Laboratories, Inc. for provision of EDCI·HClWeitere Informationen
Publikationsverlauf
Received: 03. Mai 2017
Accepted after revision: 25. Mai 2017
Publikationsdatum:
20. Juli 2017 (online)
Abstract
This report describes the total synthesis of lagerstannin C, a natural ellagitannin that has d-gluconic acid in the molecule. The study presented here is the first synthesis of the gluconic acid containing ellagitannin. The key step in the synthesis is the opening of δ-lactone through transesterification to form the corresponding benzyl ester.
Key words
total synthesis - natural products - ellagitannin - lagerstannin C - gluconic acid - transesterificationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588477.
- Supporting Information
-
References
- 1 Tanaka T. Tong H.-H. Xu Y.-M. Ishimaru K. Nonaka G.-I. Nishioka I. Chem. Pharm. Bull. 1992; 40: 2975
- 2 Perry LM. Medicinal Plants of East and Southeast Asia . MIT Press; Cambridge: 1980: 248
- 3 Khanbabaee K. Lötzerich K. Eur. J. Org. Chem. 1999; 3079
- 4 Khanbabaee K. van Ree T. Synthesis 2001; 1585
- 5 Khanbabaee K. Großer M. Eur. J. Org. Chem. 2003; 2128
- 6 Itoh T. Chika J. J. Org. Chem. 1995; 60: 4968
- 7 Michihata N. Kaneko Y. Kasai Y. Tanigawa K. Hirokane T. Higasa S. Yamada H. J. Org. Chem. 2013; 78: 4319
- 8a Haider A. Williams CK. C. R. Chim. 2011; 14: 736
- 8b Joseph CC. Regeling H. Zwanenburg B. Chittenden GJ. F. Tetrahedron 2002; 58: 6907
- 8c Kohri M. Kimura T. Shinoda Y. Taniguchi T. Nakahira T. Carbohydr. Res. 2011; 346: 2965
- 9a Bowles P. Brenek SJ. Caron S. Do NM. Drexler MT. Duan S. Dubé P. Hansen EC. Jones BP. Jones KN. Ljubicic TA. Makowski TW. Mustakis J. Nelson JD. Olivier M. Peng Z. Perfect HH. Place DW. Ragan JA. Salisbury JJ. Stanchina CL. Vanderplas BC. Webster ME. Weekly RM. Org. Process Res. Dev. 2014; 18: 66
- 9b Gratien J. Heck M.-P. Mioskowski C. Carbohydr. Res. 2008; 343: 18
Per-O-acetyl gluconic acid:
Per-O-Bn gluconic acid: