Tandem cyclization–cycloaddition reactions of rhodium generated carbenoids from α-diazo carbonyl compounds

Mehta, Goverdhan; Muthusamy, Sengodagounder

doi:10.1016/s0040-4020(02)01187-0

Cited by 228 publications

(36 citation statements)

References 162 publications

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“…[39][40][41] The ease of generating the dipole, the rapid accumulation of polyfunctionality in a relatively small molecular framework, the high stereochemical control of the subsequent [3+2]-cycloaddition, and the fair predictability of its regiochemistry have contributed to the popularity of the reaction. 42,43 When the reacting components are themselves cyclic or have ring substituents, complex multicyclic arrays, such as those contained in drugs and natural products, can be constructed in a single step.…”

Section: Rh(ii)-catalyzed Reaction Of Diazo Carbonyl Substrates For Ymentioning

confidence: 99%

Use of nitrogen and oxygen dipole ylides for alkaloid synthesis

Padwa¹

2018

Arkivoc

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As highlighted in this mini review, a growing area of interest in organic synthesis involves the use of substituted azomethine and carbonyl ylides as 1,3-dipoles for the preparation of alkaloidal natural products. Cascade reactions proceeding by an intramolecular 1,3-dipolar cycloaddition of nitrogen and oxygen dipole ylides are of particular interest to the synthetic organic community because of the increase in molecular complexity involved and the high isolated yields.

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Section: Rh(ii)-catalyzed Reaction Of Diazo Carbonyl Substrates For Ymentioning

confidence: 99%

Use of nitrogen and oxygen dipole ylides for alkaloid synthesis

Padwa¹

2018

Arkivoc

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“…[50][51][52][53][54][55] The utility of the method was first demonstrated by Ibata and co-workers in 1972, wherein Cu(acac) 2 was used as a catalyst. 56) Since Padwa and coworkers reported that the rhodium(II)-mediated cyclization/ cycloaddition reactions proceeded under much milder conditions than was common for the classic method with Cu(acac) 2 , 57) this process has been extensively studied and has represented an attractive strategy for tetrahydrofuran formation.…”

Section: Tandem Carbonyl Ylide Formation/13-dipolar Cycloaddition Apmentioning

confidence: 99%

Total Synthesis of the Squalene Synthase Inhibitor Zaragozic Acid C

Nakamura

2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Zaragozic acids and squalestatins were documented by Merck, Glaxo, and Tokyo Noko University/Mitsubishi Kasei Corporation as part of a program aimed at identifying novel inhibitors of squalene synthase, as well as farnesyl transferase. These natural products have attracted considerable attention from numerous synthetic chemists because of their therapeutic potential and novel architecture. This review highlights our total syntheses of zaragozic acid C by two convergent strategies. The key steps in our first-generation synthesis involve 1) simultaneous creation of the C4 and C5 quaternary stereocenters through the Sn(OTf) 2 -promoted aldol coupling reaction between the a a-keto ester and silyl ketene thioacetal derived from L-and D-tartaric acids, respectively; and 2) construction of the bicyclic core structure via acid-catalyzed internal ketalization under kinetically controlled conditions. The second-generation strategy relies on a tandem carbonyl ylide formation/1,3-dipolar cycloaddition approach and features elongation of the C1 alkyl side chain through an olefin cross-metathesis as well as high convergency and flexibility.

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“…[1][2][3][4][5][6][7][8][9] This is primarily due to high and various physiological activities of these heterocyclic compounds. For example, the morpholine fragment is involved as a structural element in many pharmacological drugs.…”

Section: Introductionmentioning

confidence: 99%