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Open AccessArticle

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

by Hao-yun Shi 1,2, Yang Xie 1, Pei Hu 1, Zi-qiong Guo 1,2, Yi-hong Lu 1,2, Yu Gao 1,* and Cheng-gang Huang 1,2,*
Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, China
School of Pharmacy, University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China
Authors to whom correspondence should be addressed.
Mar. Drugs 2018, 16(11), 414;
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)
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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MDPI and ACS Style

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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