Efficient strategy for the iterative synthesis of trans-fused polycyclic ether via SmI2-induced reductive intramolecular cyclization

Hori, Nobuyuki; Matsukura, Hiroko; Matsuo, Goh; Nakata, Tadashi

doi:10.1016/s0040-4020(02)00042-x

Cited by 68 publications

(45 citation statements)

References 59 publications

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“…An intramolecular 1,4-addition also played a role in the SmI 2 -induced reductive cyclization introduced in the same year by Nakata and co-workers for the generation of six-and seven-membered cyclic ethers (Scheme 21). [71] Thus, treatment of enol ether substrates 123 (n = 1) and 124 (n = 2) with SmI 2 in methanol promoted, first, single-electron reduction of the aldehyde moiety to form the presumed radicals 125 and 126, respectively. [72] Coordination between the samariumcomplexed ketyl radical oxygen atom and the carbonyl group of the proximal Michael acceptor was invoked to explain the stereoselective intramolecular 1,4-addition of the radical species to the a,b-unsaturated carbonyl moiety to form intermediate radicals 127 and 128, which proceeded to form bicycle 129 and tricycle 130, respectively.…”

Section: Synthetic Methodsmentioning

confidence: 99%

The Continuing Saga of the Marine Polyether Biotoxins

2008

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The unprecedented structure of the marine natural product brevetoxin B was elucidated by the research group of Nakanishi and Clardy in 1981. The ladderlike molecular architecture of this fused polyether molecule, its potent toxicity, and fascinating voltage-sensitive sodium channel based mechanism of action immediately captured the imagination of synthetic chemists. Synthetic endeavors resulted in numerous new methods and strategies for the construction of cyclic ethers, and culminated in several impressive total syntheses of this molecule and some of its equally challenging siblings. Of the marine polyethers, maitotoxin is not only the most complex and most toxic of the class, but is also the largest nonpolymeric natural product known to date. This Review begins with a brief history of the isolation of these biotoxins and highlights their biological properties and mechanism of action. Chemical syntheses are then described, with particular emphasis on new methods developed and applied to the total syntheses. The Review ends with a discussion of the, as yet unfinished, story of maitotoxin, and projects into the future of this area of research.

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Section: Synthetic Methodsmentioning

confidence: 99%

The Continuing Saga of the Marine Polyether Biotoxins

2008

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“…The reaction of aldehyde 16 with propane-1,3-dithiol in presence of BF 3 ·OEt 2 13 resulted in conversion of aldehyde to the 1,3-dithiane and simultaneous removal of the acetal. Diol 17 was isolated in 78% yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of C1–C20 and C21–C40 fragments of tetrafibricin

Gudipati¹,

Curran²

2011

Tetrahedron Letters

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“…Similar different reaction stereocontrol depending upon the reaction conditions was also observed by several groups during samarium diiodide-promoted coupling reaction of carbonyl compounds in the presence or absence of HMPA. [24][25][26] For further investigation of the stereoselectivity, the (Z)-isomer of olefin (31) was subjected to the coupling. Again, the desired compound (30) was obtained by the reaction of 31 with samarium diiodide in the presence of HMPA in 39% yield, as the major coupling product.…”

Section: )mentioning

confidence: 99%

Investigation of Innovative Synthesis of Biologically Active Compounds on the Basis of Newly Developed Reactions

Honda

2012

Chem. Pharm. Bull.

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Synthesis of biologically active compounds, including natural products and pharmaceutical agents, is an important and interesting research area since the large structural diversity and complexity of bioactive compounds make them an important source of leads and scaffolds in drug discovery and development. Many structurally and also biologically interesting compounds, including marine natural products, have been isolated from nature and have also been prepared on the basis of a computational design for the purpose of developing medicinal chemistry. In order to obtain a wide variety of derivatives of biologically active compounds from the viewpoint of medicinal chemistry, it is essential to establish efficient synthetic procedures for desired targets. Newly developed reactions should also be used for efficient synthesis of desired compounds. Thus, recent progress in the synthesis of biologically active compounds by focusing on the development of new reactions is summarized in this review article.

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Efficient strategy for the iterative synthesis of trans-fused polycyclic ether via SmI2-induced reductive intramolecular cyclization

Cited by 68 publications

References 59 publications

The Continuing Saga of the Marine Polyether Biotoxins

The Continuing Saga of the Marine Polyether Biotoxins

Synthesis of C1–C20 and C21–C40 fragments of tetrafibricin

Investigation of Innovative Synthesis of Biologically Active Compounds on the Basis of Newly Developed Reactions

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