a further contribution to the study of sagittamide a synthesis of a pivotal intermediate belonging to a rare l-series进一步研究贡献sagittamide关键中间体的合成属于一种罕见的l系列.pdfVIP
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a further contribution to the study of sagittamide a synthesis of a pivotal intermediate belonging to a rare l-series进一步研究贡献sagittamide关键中间体的合成属于一种罕见的l系列
Molecules 2012, 17, 7709-7721; doi:10.3390/molecule
OPEN ACCESS
molecules
ISSN 1420-3049
/journal/molecules
Article
A Further Contribution to the Study of Sagittamide A:
Synthesis of a Pivotal Intermediate Belonging to a Rare L-Series
Anne Humbert, Karen Plé, Dominique Harakat, Agathe Martinez and Arnaud Haudrechy *
Institut de Chimie Moléculaire de Reims, UMR CNRS 7312, Université de Reims, BP 1039,
F-51687 REIMS Cedex, France; E-Mails: anne.bak@hotmail.fr (A.H.); karen.ple@univ-reims.fr (K.P.);
dominique.harakat@univ-reims.fr (D.H.); agathe.martinez@univ-reims.fr (A.M.)
* Author to whom correspondence should be addressed; E-Mail: arnaud.haudrechy@univ-reims.fr;
Tel.: +33-2691-3236; Fax: +33-2691-3166.
Received: 3 May 2012; in revised form: 13 June 2012 / Accepted: 18 June 2012 /
Published: 25 June 2012
Abstract: A key saggitamide intermediate corresponding to a rare sugar framework has
been obtained. This approach should help to establish the overall configuration of more
complex structures of the sagittamide family.
Keywords: sagittamide; L-altrose; L-talose; epoxide opening; asymmetric dihydroxylation
1. Introduction
Sagittamides A–F (1–6, Figure 1) are unprecedented marine natural products isolated from an
unidentified tropical didemnid tunicate collected in Micronesia and described by Molinski [1,2]. These
compounds are characterized by an -dicarboxylic acid (C-26 or C-28) that is acylated at each
terminus by a different amino acid (L-ornithine o
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