Synthesis-Driven Structure Assignment of Marine Natural Products

A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: closed (25 April 2021) | Viewed by 7352

Special Issue Editor


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Guest Editor
Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan
Interests: marine natural products; organic synthesis; natural product chemistry

Special Issue Information

Dear Colleagues,

Marine natural products serve as an important source of chemical probes for dissecting complex biological phenomena as well as chemotherapeutics against a range of human diseases. Elucidation of the structure of natural products is a prerequisite for accurate discussion on their structure–activity relationship and mode-of-interaction with biomolecules. However, a considerable number of incorrectly assigned marine natural products are reported every year, presumably due to heavy reliance on NMR-based structure analysis. Organic synthesis, when combined with NMR spectroscopy and other analytical methods, is a powerful means for structure determination. Synthesis of appropriately designed model compounds aids the assignment of stereochemically complex natural products, and, undoubtedly, total synthesis plays an indispensable role in the establishment of their full structure.

This Special Issue aims to focus on synthesis-driven structure assignment/determination of marine natural products, including discussions on new aspects of synthetic strategies, NMR data analytics, supportive analytical methods, and innovative prediction methods, e.g., quantum chemical calculations and biosynthetic gene cluster analysis.

Prof. Dr. Haruhiko Fuwa
Guest Editor

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Keywords

  • structure elucidation
  • total synthesis
  • partial synthesis
  • configurational assignment
  • spectroscopic analysis
  • NMR chemical shift deviation analysis
  • HPLC analysis
  • quantum chemical calculations

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Published Papers (2 papers)

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Research

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18 pages, 2781 KiB  
Article
Total Synthesis and Structural Reassignment of Laingolide A
by Fusong Wu, Tao Zhang, Jie Yu, Yian Guo and Tao Ye
Mar. Drugs 2021, 19(5), 247; https://doi.org/10.3390/md19050247 - 27 Apr 2021
Cited by 5 | Viewed by 3383
Abstract
The asymmetric total synthesis of four diastereomers of laingolide A was achieved, which led to the unambiguous assignment of the stereochemistry of the natural product. The salient features of the convergent, fully stereocontrolled approach were a copper-catalysed stereospecific Kumada-type coupling, a Julia-Kocienski olefination [...] Read more.
The asymmetric total synthesis of four diastereomers of laingolide A was achieved, which led to the unambiguous assignment of the stereochemistry of the natural product. The salient features of the convergent, fully stereocontrolled approach were a copper-catalysed stereospecific Kumada-type coupling, a Julia-Kocienski olefination and an RCM/alkene migration sequence to access the desired macrocyclic enamide. Full article
(This article belongs to the Special Issue Synthesis-Driven Structure Assignment of Marine Natural Products)
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Review

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40 pages, 23667 KiB  
Review
Synthesis-Driven Stereochemical Assignment of Marine Polycyclic Ether Natural Products
by Haruhiko Fuwa
Mar. Drugs 2021, 19(5), 257; https://doi.org/10.3390/md19050257 - 29 Apr 2021
Cited by 3 | Viewed by 3313
Abstract
Marine polycyclic ether natural products have gained significant interest from the chemical community due to their impressively huge molecular architecture and diverse biological functions. The structure assignment of this class of extraordinarily complex natural products has mainly relied on NMR spectroscopic analysis. However, [...] Read more.
Marine polycyclic ether natural products have gained significant interest from the chemical community due to their impressively huge molecular architecture and diverse biological functions. The structure assignment of this class of extraordinarily complex natural products has mainly relied on NMR spectroscopic analysis. However, NMR spectroscopic analysis has its own limitations, including configurational assignment of stereogenic centers within conformationally flexible systems. Chemical shift deviation analysis of synthetic model compounds is a reliable means to assign the relative configuration of “difficult” stereogenic centers. The complete configurational assignment must be ultimately established through total synthesis. The aim of this review is to summarize the indispensable role of organic synthesis in stereochemical assignment of marine polycyclic ethers. Full article
(This article belongs to the Special Issue Synthesis-Driven Structure Assignment of Marine Natural Products)
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