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Mar. Drugs 2018, 16(11), 414; https://doi.org/10.3390/md16110414

Asymmetric Synthesis of the C15–C32 Fragment of Alotamide and Determination of the Relative Stereochemistry

1
Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, China
2
School of Pharmacy, University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China
*
Authors to whom correspondence should be addressed.
Received: 15 October 2018 / Revised: 24 October 2018 / Accepted: 24 October 2018 / Published: 30 October 2018
(This article belongs to the Special Issue Synthetic and Biosynthetic Approaches to Marine Natural Products)
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Abstract

Alotamide is a cyclic depsipetide isolated from a marine cyanobacterium and possesses a unique activation of calcium influx in murine cerebrocortical neurons (EC50 4.18 µM). Due to its limited source, the three stereocenters (C19, C28, and C30) in its polyketide fragment remain undetermined. In this study, the first asymmetric synthesis of its polyketide fragment was achieved. Four relative possible diastereomers were constructed with a boron-mediated enantioselective aldol reaction and Julia–Kocienski olefination as the key steps. Comparison of 13C NMR spectra revealed the relative structure of fragment C15–C32 of alotamide. View Full-Text
Keywords: alotamide; asymmetric synthesis; relative structural determination alotamide; asymmetric synthesis; relative structural determination
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Shi, H.-Y.; Xie, Y.; Hu, P.; Guo, Z.-Q.; Lu, Y.-H.; Gao, Y.; Huang, C.-G. Asymmetric Synthesis of the C15–C32 Fragment of Alotamide and Determination of the Relative Stereochemistry. Mar. Drugs 2018, 16, 414.

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