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Synthesis 2017; 49(22): 5003-5006
DOI: 10.1055/s-0036-1588477
paper
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Lagerstannin C: Follow-up of the Khanbabaee’s Synthesis

Yuki Kaneko
a   School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan
,
Shinnosuke Wakamori
a   School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan
,
Kazutada Ikeuchi
a   School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan
,
Kenya Ohara
a   School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan
,
Takashi Tanaka
b   Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan   Email: hidetosh@kwansei.ac.jp
,
Hidetoshi Yamada*
a   School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan
› Author AffiliationsThe 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·HCl
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Publication History

Received: 03 May 2017

Accepted after revision: 25 May 2017

Publication Date:
20 July 2017 (online)

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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 - transesterification

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588477.
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