Stereoselective synthesis of the spirocyclic core of 13-desmethyl spirolide C using an aza-Claisen rearrangement and an <i>exo</i>-selective Diels–Alder cycloaddition-Reference-Cited by-同舟云学术

Stereoselective synthesis of the spirocyclic core of 13-desmethyl spirolide C using an aza-Claisen rearrangement and an exo-selective Diels–Alder cycloaddition

Published:2023 Issue:6 Volume:21 Page:1222-1234
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Earl Andrew D. W.¹^ORCID,Li Freda F.¹²^ORCID,Ma Chao¹,Furkert Daniel P.¹²^ORCID,Brimble Margaret A.¹²^ORCID

Affiliation:

1. School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland 1010, New Zealand

2. Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3A Symonds Street, Auckland 1010, New Zealand

Abstract

This work details a novel approach to access the [7,6]-spirocyclic fragment of 13-desmethyl spirolide C. A more efficient synthesis of the key lactam dienophile is reported, and a comprehensive investigation of the Diels-Alder reaction is included.

Funder

University of Auckland

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2023/OB/D2OB01992B

Reference38 articles.

1. Portimine: a bioactive metabolite from the benthic dinoflagellate Vulcanodinium rugosum

2. Gymnodimine, a new marine toxin of unprecedented structure isolated from New Zealand oysters and the dinoflagellate, Gymnodinium sp.

3. Isolation, Structural Determination and Acute Toxicity of Pinnatoxins E, F and G

4. Characterization of Spirolides A, C, and 13-Desmethyl C, New Marine Toxins Isolated from Toxic Plankton and Contaminated Shellfish

5. Comparison of acetylcholine receptor interactions of the marine toxins, 13-desmethylspirolide C and gymnodimine

Cited by 3 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Synthesis and α-Functionalisation of Cyclic Imines;Synlett;2024-01-22

2. Biomimetic-inspired synthesis of sporochartines through Diels–Alder reaction between enantiopure (−)-sporothriolide and (+)-trienylfuranol A;Organic Chemistry Frontiers;2023

3. Synthesis of the spiroimine fragment of portimines A and B;Organic & Biomolecular Chemistry;2023