Total synthesis of (–)‐MY 336a from <scp>L</scp>‐tyrosine

Liao, Xiang Wei; Dong, Wen; Liu, Wei; Guan, Bao He; Liu, Zhan Zhu

doi:10.1002/jhet.248

Cited by 12 publications

(3 citation statements)

References 11 publications

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“…The configuration of the newly generated C-1 stereogenic center was strongly dependent on the aldehyde used. With benzyloxy acetaldehyde, the desired C-1 configuration for 1,3-syn arrangement of substituents was formed like in MY-336a 38 (56), while the opposite 1,3-anti stereochemistry, as in 57, 39 was produced in reactions with glyoxylic acid esters. 25 Chiral aldehydes such as formyl aziridine 58 37 and (S)-Garner's aldehyde ent-39 27,40 have also been used to build up rings ED of isoquinolines 59, 37 60, 40 61, 27 respectively (Chart 10).…”

Section: Pictet−spengler Cyclizationmentioning

confidence: 99%

Asymmetric Synthesis of Isoquinoline Alkaloids: 2004–2015

2016

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In the past decade, the asymmetric synthesis of chiral nonracemic isoquinoline alkaloids, a family of natural products showing a wide range of structural diversity and biological and pharmaceutical activity, has been based either on continuation or improvement of known traditional methods or on new, recently developed, strategies. Both diastereoselective and enantioselective catalytic methods have been applied. This review describes the stereochemically modified traditional syntheses (the Pictet-Spengler, the Bischler-Napieralski, and the Pomeranz-Fritsch-Bobbitt) along with strategies based on closing of the nitrogen-containing ring B of the isoquinoline core by the formation of bonds between C-N, N-C, C-N/N-C, and C-N/C-C atoms. Methods involving introduction of substituents at the C1 carbon of isoquinoline core along with syntheses applying various biocatalytic techniques have also been reviewed.

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Section: Pictet−spengler Cyclizationmentioning

confidence: 99%

Asymmetric Synthesis of Isoquinoline Alkaloids: 2004–2015

2016

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“…A number of measurements of stability constants of the amino acids (15) , 2mercaptobenzothiozole, 2-amino-Pyrano-pyrazole (16) complexes have been reported by Potentiometric techniques. Benzil-2, 4-dinitro phenyl hydrazine pyrazole complexes of La (III), Cr (III), Co (II) and Cu (II) Have been also reported (17) .…”

Section: Introductionmentioning

confidence: 99%

Determination of the Stability Constants for some First Transition Elements Complexes with 3-(2- hydroxyl phenyl ) -2 – Pyrazoline In Aqueous Solution

S.Maroof,

Mtaab,

W. Mohy

2013

ETJ

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Transition metal complexes Cr(III) , Fe(III) , Co(II) , Ni(II) & Cu(II) with 3-(2hydroxy phenyl ) -2-pyrazoline have been prepared and characterized in aqueous solution. The complexes were characterized by infrared (IR), UV-visible & molar conductivity measurements. The bidentate ligand was bonded from one of the nitrogen atoms of pyrazolien & oxygen atom phenoxide group. The molecular structure for the complexes was proposed. The stability constants of these complexes were found by measuring electric molar conductivity in different concentrations was also found. The determined values of the prepared complexes increases according to the following sequence:

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“…Some of these compounds show as a potent endothelin-A selective receptor antagonist. On the other hand, biologically important disubstituted tetrahydroisoquinolines display β-adrenergic receptor antagonist, antitumor, , and antimicrobial activities.…”

mentioning

confidence: 99%

Copper Catalyzed One-Pot Three-Component Imination–Alkynylation–aza-Michael Sequence: Enantio- and Diastereoselective Syntheses of 1,3-Disubstituted Isoindolines and Tetrahydroisoquinolines

2019

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An enantio- and diastereoselective syntheses of 1, 3-disubstituted isoindolines and tetrahydroisoquinolines via CuI-Pybox-diPh catalyzed one-pot imination–alkynylation–aza-Michael sequence has been reported. The three-component reaction produces one C–C and two C–N bonds sequentially with high yield (up to 92%), enantioselectivity (up to 99%), and diastereoselectivity (up to 9:1) in a single operation. Furthermore, the synthetic utility of the product has been demonstrated by LiAlH4 reduction of ester and hydrogenation of alkyne functionality without losing the stereoselectivity.

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Total synthesis of (–)‐MY 336a from L‐tyrosine

Cited by 12 publications

References 11 publications

Asymmetric Synthesis of Isoquinoline Alkaloids: 2004–2015

Asymmetric Synthesis of Isoquinoline Alkaloids: 2004–2015

Determination of the Stability Constants for some First Transition Elements Complexes with 3-(2- hydroxyl phenyl ) -2 – Pyrazoline In Aqueous Solution

Copper Catalyzed One-Pot Three-Component Imination–Alkynylation–aza-Michael Sequence: Enantio- and Diastereoselective Syntheses of 1,3-Disubstituted Isoindolines and Tetrahydroisoquinolines

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