Total Synthesis of Maoecrystal V

Zhang, Wei-Bin; Lin, Guang; Shao, Wang; Gong, Jianxian; Yang, Zhen

doi:10.1002/asia.201403228

Cited by 14 publications

(9 citation statements)

References 65 publications

(37 reference statements)

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“…The total synthesis of maoecrystal V has been described. 146 The helikaurolides A-D which were obtained from Helianthus annuus var n .arianna, have been assigned 147 structures based on a combination of a sesquiterpene lactone (helivypolide L) and an ent-kauranoic acid.…”

Section: Tetracyclic Diterpenoidsmentioning

confidence: 99%

Diterpenoids of terrestrial origin

Hanson

2013

Nat. Prod. Rep.

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Section: Tetracyclic Diterpenoidsmentioning

confidence: 99%

Diterpenoids of terrestrial origin

Hanson

2013

Nat. Prod. Rep.

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“…Additionally, some examples report the creation of four cycles and three or four stereogenic centers (Scheme 45). 157,158 respectively. A regioselective (5+2) cycloaddition process was used for the formation of polyether furanic cores starting from terminal alkenes and the 3-oxido-pyrilium betaine prepared in situ.…”

Section: Scheme 44: Thf Synthesis By Acetal Reductionmentioning

confidence: 97%

“…157 A mixture of endo and exo-compounds were obtained in addition with another regioisomer of the exo-product coming from previous step.…”

Section: Scheme 46: Regioselective (5+2) Cycloadditionsmentioning

confidence: 99%

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

et al. 2016

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Mousseron. His research interests include the total synthesis of oxygenated cyclic and non cyclic metabolites of polyunsaturated fatty acids, mainly leukotrienes, iso-, phyto-and neuroprostanes, as well as dihydroxylated PUFAs and more recently lipophenols and the understanding of the role of such bioactive lipids and lipophenols by developing collaborations with chemists, biochemists, biologists and clinicians across the world. Jean-Marie Galano studied chemistry at Paul Cézanne Université Marseille and obtained his PhD under the supervision of Honoré Monti in 2001. He then moved to the University of Oxford to pursue a postdoctoral fellowship with David H. Hodgson on the development of new methods for the total synthesis of natural products. In October 2005 he joined the CNRS as a Chargé de Recherche at Université of Montpellier. His research focuses on the total synthesis and discovery of new lipid metabolites, and to discover their potential implications in human health. AbstractMany natural products contain tetrahydrofuran (THF) moieties. Those molecules, often biologically active, may be structurally diverse, e.g. cis or trans THF, mono-, di-, tri-or tetrasubstituted on the furan ring. Thus, the construction of THF is of great interest for the community of organic chemists; especially in developing new methodologies, and applying them in the total synthesis of natural products. The aim of this review is to report recent advances in the field of THF synthesis, as well as the application of these methods to the synthesis of bioactive compounds.

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“…Catalytic carbene transfer reactions based on diazo compounds provide versatile, atom-economical approaches for organic synthesis . In addition to C–C bond formation, diazo reagents provide an important approach in the construction of heteroatom–carbon bonds. − In particular, the insertion of carbenes from diazo esters into the N–H bonds of amines, using transition-metal catalysts, provides an effective and direct synthesis of amino acid derivatives and biologically important heterocycles. − A variety of catalysts have been developed for N–H insertion, including copper bronze, Rh 2 (OAc) 4 , Fe(III) , and Ru(II) porphyrin complexes, , and Fe(III) corroles . Theoretical and experimental approaches have been employed to examine the mechanism of N–H insertion with diazo esters.…”

Section: Introductionmentioning

confidence: 99%

Reactivity Comparison of Primary Aromatic Amines and Thiols in E–H Insertion Reactions with Diazoacetates Catalyzed by Iridium(III) Tetratolylporphyrin

2017

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A detailed kinetic study is described for the insertion of carbenes from methyl diazoacetate into the N–H bond of aniline, using Ir(TTP)CH3 (TTP = tetratolylporphyrinato) as a catalyst. Aniline strongly coordinates to the Ir center with a binding constant of K = (2.5 ± 0.5) × 104 at 296 K, forming an inactive hexacoordinate complex, (aniline)Ir(TTP)CH3. The rate of N–H insertion is first order in both diazo ester and catalyst. When the true amount of active, five-coordinate Ir(TTP)CH3 is taken into account, the insertion rate is found to be independent of the aniline concentration. This indicates that the rate-limiting step in the catalytic cycle occurs prior to the nucleophilic attack of aniline on an Ir carbene complex to generate a coordinated ylide. Thus, with N–H insertion catalyzed by Ir(TTP)CH3, aniline is both a strong ligand and a potent nucleophile. This is in contrast to the analogous catalytic insertion of carbenes into S–H bonds. p-Toluenethiol is a more weakly binding ligand toward Ir(TTP)CH3 (K = 680 ± 20 at 296 K). Moreover, the rate of S–H insertion is first order in diazo reagent, catalyst, and thiol concentrations. In this case, the slow step is nucleophilic attack of the thiol on the Ir carbene complex to form a coordinated sulfonium ylide intermediate. In comparison to aniline, p-toluenethiol is a weaker ligand and a poorer nucleophile. The consequence of these differences is that the rate of aniline attack on the carbene intermediate is much faster than the rate of formation of the intermediate carbene complex; whereas the rate of nucleophilic addition of the thiol is slower that the rate of carbene complex formation.

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Total Synthesis of Maoecrystal V

Cited by 14 publications

References 65 publications

Diterpenoids of terrestrial origin

Diterpenoids of terrestrial origin

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

Reactivity Comparison of Primary Aromatic Amines and Thiols in E–H Insertion Reactions with Diazoacetates Catalyzed by Iridium(III) Tetratolylporphyrin

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