Sterically crowded cyclohexanes - 81). Synthesis, crystal structure, conformation and dynamics of pentaspiro[2.0.2.0.2.0.2.0.2.1]hexadecane, pentaspiro[3.0.2.0.3.0.2.0.3.1]- nonadecane and pentaspiro[3.0.3.0.3.0.3.0.3.1] heneicosane

Fitjer, Lutz; Klages, Ulrich; Wehle, Detlef; Giersig, Manfred; Schormann, N.; Clegg, William; Stephenson, David S.; Binsch, Gerhard

doi:10.1016/s0040-4020(01)85832-4

Cited by 14 publications

(5 citation statements)

References 8 publications

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“…1) 3 and spiranes. 4 Some of the spiro compounds have been utilized as building blocks in thermotropic liquid crystalline materials which in turn are used in optical devices. 5 In connection with the synthesis of unsymmetrical benzoannelated fenestranes such as 1, we need a viable route to spirobiindanediones 6.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of spiro-indanes by cycloaddition strategy

Kotha

Ethirajan

2001

J. Chem. Soc., Perkin Trans. 1

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Section: Introductionmentioning

confidence: 99%

Synthesis of spiro-indanes by cycloaddition strategy

Kotha

Ethirajan

2001

J. Chem. Soc., Perkin Trans. 1

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“…crinipellin-A, laurenene) 3 and spirocaracolitone A 2 4 have shown to posses spiro-linkage as a structural element. 5 Among non-natural products [5.5.5.5]fenestrane 3, 6 spiranes, 7 and coronane 4 posses the spiro-linkage 8a,b as a crucial unit.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of spiro-cyclics via ring-closing metathesis

Kotha¹,

Ethirajan²

2003

Arkivoc

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“…2 Hudlicky has remarked that generation of a spiro center is a highly difficult task because it involves the creation of a quaternary center. 3 Many intricate compounds, such as fredericamycin, 4 fenestrindane 5 (Figure 1), alicyclic [5.5.5.5]fenestrane, 6 and spiranes, 7 contain the spiro linkage as a core structural element. There are several approaches to synthesize spirocycles.…”

mentioning

confidence: 99%

Diversity-Oriented Approach to Novel Spirocyclics via Enyne Metathesis, Diels-Alder Reaction, and a [2+2+2] Cycloaddition as Key Steps

Kotha

Ali

Tiwari

2013

Synlett

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A simple protocol for the synthesis of indane-based spirocyclics has been developed via enyne metathesis, Diels-Alder reaction, and a [2+2+2] cycloaddition as key steps starting from indane-1,3-dione. The key diene building block was assembled by enyne metathesis. In this sequence, rongalite is used as a green reagent to prepare the sultine intermediate, which is a useful precursor to generate the transient diene.Indane derivatives 1 are useful building blocks for the synthesis of several natural and non-natural products. 2 Hudlicky has remarked that generation of a spiro center is a highly difficult task because it involves the creation of a quaternary center. 3 Many intricate compounds, such as fredericamycin, 4 fenestrindane 5 (Figure 1), alicyclic [5.5.5.5]fenestrane, 6 and spiranes, 7 contain the spiro linkage as a core structural element. There are several approaches to synthesize spirocycles. 8 These methods include alkylation, 9 transition-metalbased strategies, 10 rearrangement-based approaches, 11 radical-mediated procedures, 12 and ring-closing metathesis. 13 However, some of these methods have severe limitations due to functional-group incompatibility and may also be restricted to a limited substitution pattern. Therefore, there remains a need to design new and simple synthetic strategies to spirocyclics where the newly generated functionality at the end of the sequence can be used for additional synthetic transformations. Several intricate natural and non-natural products have been synthesized using an atom-economic ring-closing enyne metathesis as a key step. 14 In connection with our interest to generate new synthetic methods to spirocyclics, 8f we had shown that the diene building block 3 can provide linearly annulated spiro indane derivatives with various dienophiles such as dimethyl acetylenedicarboxylate 4 when the aromatized product 5 was obtained directly under toluene reflux conditions. 16d Alternatively, a [2+2+2]-cycloaddition sequence was also applied to synthesize linearly annulated indane-based spiro derivatives containing silicon substituents (Scheme 1).To expand the building-block approach 8c to various spirocyclics, we have identified that the diene building blocks 9 and 10 are suitable to generate a library of spiro indane Scheme 1 Indane-based spirocyclic compounds by [4+2] and [2+2+2] approach O O

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Sterically crowded cyclohexanes - 81). Synthesis, crystal structure, conformation and dynamics of pentaspiro[2.0.2.0.2.0.2.0.2.1]hexadecane, pentaspiro[3.0.2.0.3.0.2.0.3.1]- nonadecane and pentaspiro[3.0.3.0.3.0.3.0.3.1] heneicosane

Cited by 14 publications

References 8 publications

Synthesis of spiro-indanes by cycloaddition strategy

Synthesis of spiro-indanes by cycloaddition strategy

Synthesis of spiro-cyclics via ring-closing metathesis

Diversity-Oriented Approach to Novel Spirocyclics via Enyne Metathesis, Diels-Alder Reaction, and a [2+2+2] Cycloaddition as Key Steps

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