Related Experiment Video
Updated: Jun 5, 2025

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
Convergent and Scalable Second-Generation Synthesis of the Fully Functionalized HIJKLMN-Ring Segment of Caribbean
Makoto Sasaki1, Miyu Ohba1, Ako Murakami1
1Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
Abstract:
A highly convergent and scalable second-generation synthesis of the fully functionalized HIJKLMN-ring segment of Caribbean ciguatoxin C-CTX-1, the primary toxin responsible for ciguatera fish poisoning in the Caribbean Sea and the Northeast Atlantic regions, has been accomplished. Key aspects of the synthetic approach include the efficient syntheses of the HI- and KLM-ring fragments on gram scales, a convergent fragment coupling toward the HIJKLM-ring skeleton based on the Suzuki-Miyaura coupling strategy, and optimized iron hydride-catalyzed hydrogen atom transfer-mediated olefin coupling conditions for constructing the N-ring.
Related Concept Videos
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Cycloaddition Reactions: Overview
Stereoisomerism of Cyclic Compounds
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...

