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Total Synthesis of Natural Products and Their Analogues

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (30 April 2025) | Viewed by 746

Special Issue Editor


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Guest Editor
School of Chemical Sciences, The University of Auckland, Auckland 1010, New Zealand
Interests: medicinal chemistry; natural products total synthesis; asymmetric synthesis; bioactive natural products; polymeric materials; anticancer treatments; synthesis from biowaste-derived materials; isotopically labelled materials
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Special Issue Information

Dear Colleagues,

The diversity of natural products, whether from terrestrial, marine, or microbial origin, continues to challenge synthetic chemists. Synthesis is frequently conducted to confirm the molecular structures of isolated natural products, and to challenge chemists developing new synthetic methodologies or exploring the massive array of biological activities natural products can induce. With natural products commonly found as single enantiomers, asymmetric approaches are frequently utilized to define the stereochemistry and to determine, or confirm, the absolute configurations of natural products. In this regard, total synthesis plays an important role as a means to achieve the unambiguous assignment of chemical structure. Additionally, total synthesis provides access to material for biological testing which may not be available from the natural source itself. Furthermore, total synthesis develops methods that can then be used to access unnatural analogues, often with the aim of improving biological properties.

Prof. Dr. David Barker
Guest Editor

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Keywords

  • total synthesis
  • natural products
  • asymmetric synthesis
  • structure determination
  • synthetic methodology
  • analogue synthesis

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Published Papers (1 paper)

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Research

16 pages, 2146 KiB  
Article
Investigation of Dearomatizing Spirocyclizations and Spirocycle Functionalization En Route to Spirocalcaridines A and B—Some Trials and Tribulations
by Ravi P. Singh, Delphine Gout, James X. Mao, Peter Kroll and Carl J. Lovely
Molecules 2025, 30(5), 1143; https://doi.org/10.3390/molecules30051143 - 3 Mar 2025
Viewed by 546
Abstract
Spirocalcaridines A and B are among the most challenging members of the marine invertebrate-derived Leucetta alkaloids. Approaches to the construction and elaboration of the highly compact spirocyclic core are described. The synthesis of tricyclic guanidine via tandem oxidative amination dearomatizing spirocyclization (TOADS) using [...] Read more.
Spirocalcaridines A and B are among the most challenging members of the marine invertebrate-derived Leucetta alkaloids. Approaches to the construction and elaboration of the highly compact spirocyclic core are described. The synthesis of tricyclic guanidine via tandem oxidative amination dearomatizing spirocyclization (TOADS) using hypervalent iodine set the stage for total synthesis via the migration of the C4/C8 double bond to the C4/C5 position, followed by oxidation. The undesired but not surprising propensity of the spirocyclic cyclohexadienone to undergo rearrangement to the phenol hindered the desired olefin migration. Furthermore, initial efforts to install the oxidation sequentially, first at C5 and then at C4 in the complete carbon skeleton, were fraught with unforeseen challenges and unusual outcomes. In addition, the scope and limitations of hypervalent iodine-mediated tandem oxidative dearomatizing spirocyclization on various substrates were explored. Urethanes and thiourethanes underwent spirocyclization with an excellent yield, whereas the reaction with allylic substrates and species lacking the p-methoxy substituent did not proceed. Attempts to prepare other guanidine precursors are briefly discussed. Full article
(This article belongs to the Special Issue Total Synthesis of Natural Products and Their Analogues)
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