Practical route to the left wing of CTX1B and total syntheses of CTX1B and 54-deoxyCTX1B.
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Summary
A reliable route for constructing the left wing of CTX1B, which possesses the acid/base/oxidant-sensitive bisallylic ether moiety, by a 6-exo radical cyclization/ring-closing metathesis strategy is reported.
- Type
- article
- Published
- 2015-02-02
- Cited by
- 12
- References
- 107
- Access
- Open access
- OpenAlex
- https://openalex.org/W25529606
- Semantic Scholar
- https://api.semanticscholar.org/CorpusID:8908287
Keywords
Humanities, Art
References
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- Critical importance of the nine-membered F ring of ciguatoxin for potent bioactivity: total synthesis and biological evaluation of F-ring-modified analogues.
- Total Synthesis of Ciguatoxin CTX3C
- SmI2-induced reductive cyclization of optically active β-alkoxyvinyl sulfoxides with aldehyde
- Production of monoclonal antibodies for sandwich immunoassay detection of ciguatoxin 51-hydroxyCTX3C.
- Evaluation of tributylgermanium hydride as a reagent for the reductive alkylation of active olefins with alkyl halides
- Highly stereoselective approaches to .alpha.- and .beta.-C-glycopyranosides
- A Concise Route to Two Distinct E‐Ring Structures of Ciguatoxins.
- Use of monoclonal antibodies as an effective strategy for treatment of ciguatera poisoning.
- Stereoselective synthesis of the left wing of Caribbean ciguatoxin
- Efficient chirality transfer in the SmI2-mediated cyclization of aldehydo beta-alkoxyvinyl sulfoxides: asymmetric synthesis of 3-hydroxyoxanes.
- Synthesis and Applications of RuCl2(CHR‘)(PR3)2: The Influence of the Alkylidene Moiety on Metathesis Activity
- Internal activation of acrylate-type dienophiles in Diels-Alder reactions
- Synthesis of the EF-ring of ciguatoxin 3C based on the [2,3]-Wittig rearrangement and ring-closing olefin metathesis.
- Structural Elucidation of Ciguatoxin Congeners by Fast-Atom Bombardment Tandem Mass Spectroscopy
- Use of 1,2-dichloro 4,5-dicyanoquinone (DDQ) for cleavage of the 2-naphthylmethyl (NAP) group
- Lanthanides in organic chemistry. 1. Selective 1,2 reductions of conjugated ketones
- Stereoselective Synthesis of Caribbean Ciguatoxin M‐Ring Using [2 + 2] Photocyclization.
Cited by
- The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2015 ☆
- Total synthesis and related studies of large, strained, and bioactive natural products
- Thirty Years of (TMS)3SiH: A Milestone in Radical-Based Synthetic Chemistry.
- Rationally Designed Synthetic Haptens to Generate Anti-Ciguatoxin Monoclonal Antibodies, and Development of a Practical Sandwich ELISA to Detect Ciguatoxins
- Chemical Degradation-Inspired Total Synthesis of the Antibiotic Macrodiolide, Luminamicin.
- Convergent and Scalable Synthesis of the ABCDE-Ring Fragment of Caribbean Ciguatoxin C-CTX-1.
- Evaluation of relative potency of calibrated ciguatoxin congeners by near-infrared fluorescent receptor binding and neuroblastoma cell-based assays.
- Synthesis of the I–K Fused Polyether Array of CTX3C and Related Ciguatoxins by Use of a Gold-Catalyzed Cyclization Reaction
- Sensitive Detection of Ciguatoxins Using a Neuroblastoma Cell-Based Assay with Voltage-Gated Potassium Channel Inhibitors
- Convergent Total Synthesis of Caribbean Ciguatoxin C‑CTX1 and Its C3-Epimer
- Ciguatoxin Detection Methods and High‐Throughput Assays
- Ciguatoxin and Ciguatera
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