Synthesis of the common FGHI-ring part of ciguatoxins

Takizawa, Ayumi; Fujiwara, Kenshu; Doi, Eriko; Murai, Akio; Kawai, Hidetoshi; Suzuki, Takanori

doi:10.1016/j.tetlet.2005.11.085

Cited by 13 publications

(1 citation statement)

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“…Inoue and Hirama have also reported the synthesis of an A→E ring fragment that employs an acyl radical cyclization for the synthesis of the D ring. 35 Other papers on synthetic studies directed toward the ciguatoxins include a synthesis of the FGHI ring domain 36 and a synthesis of the H→M ring system. 37 In synthetic studies on yessotoxin, a convergent synthesis of the CDEF ring fragment that employs a-cyanoether chemistry has been reported, 38 as has a synthesis of the ABC and IJ ring fragments.…”

Section: Polyethersmentioning

confidence: 99%

Marine natural products: synthetic aspects

Morris

Phillips

2008

Nat. Prod. Rep.

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Section: Polyethersmentioning

confidence: 99%

Marine natural products: synthetic aspects

Morris

Phillips

2008

Nat. Prod. Rep.

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Hydrozirconation of Alkynes

Milligan,

Hammill,

Crocker

et al. 2023

Organic Reactions

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Since the first preparation of organozirconocenes from alkenes and alkynes in 1972, hydrozirconation has become one of the most commonly used stoichiometric methods to convert readily available starting materials into reactive but stable organometallic intermediates. A broad range of subsequent transformations may be employed to convert organozirconocenes in situ into high‐value functionalized products, often with the strategic formation of one (or several) new carbon–carbon bonds. This chapter focuses on the hydrozirconation of terminal and internal alkynes, and the subsequent synthetic transformations of the resulting alkenylzirconocenes. Zirconocene hydrochloride, Cp 2 Zr(H)Cl, is most frequently employed for the hydrozirconation step and can be used as a reagent or prepared in situ. Subsequent reactions of alkenylzirconocenes include additions to inorganic electrophiles such as halogens, as well as in situ ligand transfers to other metals, such as palladium and zinc, that further expand the range of accessible bond formations. The initial discussion focuses on the mechanism and stereochemical considerations, and on the steric and electronic factors that determine the regiochemistry of the either kinetically or thermodynamically controlled hydrozirconation. The “Scope and Limitations” section presents information on functional group compatibilities and is organized by the type of synthetic transformation of alkenylzirconocenes. Representative applications of the hydrozirconation of alkynes are showcased in syntheses of natural products, comparisons to alternative methods for the hydrometallation of alkynes. The goal of this chapter is to demonstrate the significance of hydrozirconation in organic synthesis, including the utility of the stoichiometric zirconium organometallics obtained from alkyne substrates, and to provide inspiration for the future development of new synthetic methods and strategies.

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Dinophyceae (Dinoflagellates)

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: General Aspects Classification of Dinoflagellates Photosynthetic Pigments Sulfated Exopolysaccharides Sterols Fatty Acids Glycolipids Amphidinols and other Polyhydroxylated Polyenic Derivatives Toxic Proliferations: Endotoxins and Exotoxins Main Types of Dinoflagellate Toxins Cyclic Polyethers Okadaic Acid and Derivatives Toxic Macrolides: Amphidinolides, Caribenolide, Goniodomin A , Hoffmanniolide Complexity of the Biosynthesis of Polyketides Saxitoxin and its Derivatives Nitrogenous Toxins with Imine Function Zooxanthellatoxins ( ZTs ) and other Nitrogenous Toxins Pfiesteria piscicida : A Particularly Toxic Dinoflagellate Sulfur‐Containing Derivatives Phosphorus Derivatives and other Unusual Compounds

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Synthesis of the common FGHI-ring part of ciguatoxins

Cited by 13 publications

References 65 publications

Marine natural products: synthetic aspects

Marine natural products: synthetic aspects

Hydrozirconation of Alkynes

Dinophyceae (Dinoflagellates)

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