Construction of quaternary centres for natural polycycles: The Pauson–Khand approach

Arnáiz, Eduardo; Blanco‐Urgoiti, Jaime; Abdi, Delbrin; Domı́nguez, Gema; Castells, Javier Pérez

doi:10.1016/j.jorganchem.2008.04.023

Cited by 17 publications

(2 citation statements)

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“…In previous studies we have succeeded in making these kinds of substrates reactive by adding an additional rhodium catalyst to the reaction. [17] Thus, when 32 was refluxed in toluene in the presence of molecular sieves and with 5 % [Rh(PPh 3 )ClCO], we obtained the desired product 33 in 30 % yield along with another product which could not be completely purified. These products appeared in the crude mixture as a 3:2 mixture.…”

Section: Resultsmentioning

confidence: 95%

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Combination of RCM and the Pauson–Khand Reaction: One‐Step Synthesis of Tricyclic Structures

et al. 2008

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The combination of ring‐closing metathesis (RCM) followed by an intramolecular Pauson–Khand reaction gives direct entry to tricyclic compounds. The RCM was carried out on a hexacarbonylcobalt‐complexed alkyne, this complex acting as a protecting group against enyne metathesis. The procedure was studied for dienynes containing heteroatoms and allows the building of [6,5,5] and [7,5,5] tricyclic systems. The feasibility of the process depends strongly on the nature of the substrate.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Section: Resultsmentioning

confidence: 95%

“…We envisioned that this tetracyclic framework could be created by RCM/PKR starting from dienyne 31. Thus, compound 29 [17] was oxidized to the corresponding aldehyde 30, which was transformed into amine 31 by reductive amination. Then the amine group was protected and the triple bond was complexed to cobalt.…”

Section: Resultsmentioning

confidence: 99%

Combination of RCM and the Pauson–Khand Reaction: One‐Step Synthesis of Tricyclic Structures

et al. 2008

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Total Synthesis of the Hamigerans

Xue

Wang

et al. 2016

Angewandte Chemie

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The first total synthesis of hamigerans D, G, L, and N-Q has been accomplished. Aconvergent approachwas used to build the basic tricarbocyclic ring system bearing a5 -6-6 structure.Asequence of oxidative cleavage,homologation, and ring regeneration provided access to the 5-7-6 skeleton of hamigeran G. Based on the biogenetic hypothesis,elegant and highly efficient biomimetic transformations of hamigeran G into hamigerans D, N-Q, and Lw ere achieved. Scheme 4. Total synthesis of 6.X-ray structures are shown. Thermal ellipsoidss hown at 50 %probability. [24] DMP = Dess-Martin periodinane, NMO = 4-methyl-morpholin-4-oxide, PTSA = p-toluenesulfonic acid, Py = pyridine.Scheme 5. Biomimetic transformation of 6 into 8 and its 18-epi isomer.

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