Transition Metal Catalyzed Cycloadditions:  An Intramolecular [4 + 4] Cycloaddition Strategy for the Efficient Synthesis of Dicyclopenta[<i>a</i>,<i>d</i>]cyclooctene 5−8−5 Ring Systems

Wender, Paul A.; Nuss, John M.; Smith, David B.; Suárez‐Sobrino, Ángel L.; Vagberg, J. O.; Decosta, D. L.; Bordner, Jon

doi:10.1021/jo970841x

Cited by 103 publications

(29 citation statements)

References 34 publications

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“…233 Nickel-mediated oxidative cyclization of two π-components (e. g. ketone and olefin) is of particular significance, since the resulting formation of a nickelacycle is believed to be an intermediate step in several useful transformations. 234 A number of these processes involve as a third component a main group organometallic entity. 235 In this area, two recent studies from the groups of Schlegel and Montgomery (Scheme 40) 236 and Ogoshi and Kurosawa 237 deal with the role of ZnMe2 and AlMe3, respectively, in promoting the oxidative cyclization reaction.…”

Section: Tm-ch3 As Intermediates In Catalysismentioning

confidence: 99%

Methyl Complexes of the Transition Metals

Campos

López‐Serrano

Peloso

et al. 2016

Chemistry A European J

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Organometallic chemistry can be considered as a wide area of knowledge that combines concepts of classic organic chemistry, i.e. based essentially on carbon, with molecular inorganic chemistry, especially with coordination compounds. Transition metal methyl complexes probably represent the simplest and most fundamental way to view how these two major areas of chemistry combine and merge into novel species with intriguing features in terms of reactivity, structure, and bonding. Citing more than 500 bibliographic references, this review aims to offer a concise view of recent advances in the field of transition metal complexes containing M-CH3 fragments. Taking into account the impressive amount of data that are continuously provided by organometallic chemists in this area, this review is mainly focused on results of the last 5 years. After a panoramic overview on M-CH3 compounds of groups 3 to 11 which includes the most recent landmark findings in this area, two further sections are dedicated to methyl-bridged complexes and reactivity.

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Section: Tm-ch3 As Intermediates In Catalysismentioning

confidence: 99%

Methyl Complexes of the Transition Metals

Campos

López‐Serrano

Peloso

et al. 2016

Chemistry A European J

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“…The structural complexity and important biological activity of terpenoids with dicyclopenta[a,d]- cyclooctane carbon skeletons attracted a great deal of attention from synthetic chemists [ 7 , 8 , 9 , 10 ]. The majority of work has focused on the methodology for construction of eight-membered ring systems [ 11 , 12 ].…”

Section: Introductionmentioning

confidence: 99%

Studies Towards the Total Synthesis of Di- and Sesterterpenes with Dicyclopenta[a,d]cyclooctane Skeletons. Three-component Approach to the A/B Rings Building Block

Michalak

Wicha

2005

Molecules

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Sesqui- and sesterterpenes of ophiobolin and fusicoccin families are important synthetic targets because of complexity of structure and potentially useful physiological activities, including anti-tumor activity. A synthesis of versatile building blocks for these terpenoids is described. Cyclopenta[8]annulene rings system with properly dislocated substituents was constructed using as key steps ring closing metathesis reaction and Wagner - Meerwein rearrangement. Ring closing metathesis reaction leading to cyclopenta[8]annulene was studied in detail.

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“…The eight‐membered ring‐forming transformation of 19 , 20 , the key step of this total synthesis, was accomplished in 67 % yield and gave a single diastereomer (Scheme ) 20a. Wender also utilized this [(4+4)] reaction to construct the 5/8/5 skeleton of ophiobolin F (Scheme ) 20b. The key cycloaddition was accomplished by treatment of bis‐diene 21 with 10 mol % [Ni(cod) 2 ] and 20 mol % triphenylphosphine in toluene at 60 °C, followed by desilylation, affording bicyclic cyclooctadiene 22 in 60 % yield.…”

Section: [4+4] Cycloadditionsmentioning

confidence: 99%

Transition‐Metal‐Catalyzed Cycloadditions for the Synthesis of Eight‐Membered Carbocycles

Wang

2010

Chemistry An Asian Journal

163

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Eight-membered carbocycles are found in a wide variety of natural products that exhibit a broad range of biological and medicinal activities (cf. the most potent anticancer drug, taxol). However, the synthesis of eight-membered carbocycles is quite challenging as traditional approaches are met with entropic and enthalpic penalties in the ring-forming transition states. These negative effects can be totally or partially avoided with the implementation of transition-metal-catalyzed/mediated cycloadditions. In this Focus Review, examples of elegant and efficient metal-catalyzed and some metal-mediated cycloadditions (including Ni- catalyzed [4+4] and Rh-catalyzed [4+2+2] and [5+2+1] reactions) are presented to illustrate this. Application of these cycloaddition reactions in total synthesis is also presented to show the significance of these reactions in addressing challenges in natural product synthesis.

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Transition Metal Catalyzed Cycloadditions: An Intramolecular [4 + 4] Cycloaddition Strategy for the Efficient Synthesis of Dicyclopenta[a,d]cyclooctene 5−8−5 Ring Systems

Cited by 103 publications

References 34 publications

Methyl Complexes of the Transition Metals

Methyl Complexes of the Transition Metals

Studies Towards the Total Synthesis of Di- and Sesterterpenes with Dicyclopenta[a,d]cyclooctane Skeletons. Three-component Approach to the A/B Rings Building Block

Transition‐Metal‐Catalyzed Cycloadditions for the Synthesis of Eight‐Membered Carbocycles

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