Asymmetric Total Synthesis of Pseurotin A

Hayashi, Yujiro; Shoji, Mitsuru; Yamaguchi, Shinpei; Mukaiyama, T.; Yamaguchi, Junichiro; Kakeya, Hideaki; Osada, Hiroyuki

doi:10.1021/ol034630s

Cited by 53 publications

(32 citation statements)

References 25 publications

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“…Its absolute configuration was determined by X-ray diffraction analysis of a dibromo derivative [ 1 ]. Most of the other γ-lactams were determined by asymmetric total synthesis [ 5 , 6 , 7 , 8 , 9 , 10 ] and the modified Mosher’s method [ 11 , 12 ]. Previously, we reported that all stereoisomers of FD-838 showed an association between the CD Cotton effect and the absolute configuration of the chiral centers in γ-lactam [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

Assignment of the CD Cotton Effect to the Chiral Center in Pseurotins, and the Stereochemical Revision of Pseurotin A2

et al. 2016

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Pseurotins A1 (1) and A2 (2) were isolated from a culture broth of the fungal strain Aspergillus fumigatus WFZ-25 as stereoisomers of pseurotin A (3) in 2011. We also isolated 1 and 2 together with 3 from A. fumigatus OUPS-T106B-5 separated from the marine fish Mugil cephalus. In this study, we re-examined the stereochemistry of 1 and 2 using chemical transformation and the CD spectra, and found the relationship between the CD Cotton effect and the absolute configurations of 1 and 2, which led us to revise the stereostructure of pseurotin A2.

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Section: Introductionmentioning

confidence: 99%

Assignment of the CD Cotton Effect to the Chiral Center in Pseurotins, and the Stereochemical Revision of Pseurotin A2

et al. 2016

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“…Multiple transformations starting from the intermediate 395 subsequently furnished the final natural products pseurotin A and 8-O-demethylpseurotin A (Scheme 84). [79] In 2007, Crone and Kirsch reported two reactions utilizing 2-alkynyl-2-silyloxy carbonyl compounds for the synthesis of 4iodo-3(2H)-furanones (Scheme 85). The first reaction follows an electrophilic cyclization pathway induced by N-iodosuccinimide while the second proceeds as a gold catalyzed tandem reaction followed by 1,2-migration.…”

Section: Methods For the Synthesis Of 245-trisubstituted-3(2h)-furamentioning

confidence: 99%

Synthesis of 3(2H)‐Furanones: A Review

2020

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“…Hayashi's group achieved the total syntheses of azaspirene (133), 66 pseurotin A (134), 67 and synerazol (137) 68…”

Section: -1 Hayashi's Total Syntheses Of (−)-Azaspirene Pseurotin a And Synerazolmentioning

confidence: 99%

Highly Oxidized γ-Lactam-Containing Natural Products: Total Synthesis and Biological Evaluation

Kobayashi¹,

Tanaka²,

Kogen³

2021

HETEROCYCLES

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γ-Lactam is a ubiquitous structure found in the natural products. A number of highly oxidized γ-lactam-containing natural products are produced by various fungi. These compounds often show a wide range of biological activities because their multiple internal reaction sites, which arise from the high oxidation state of the compounds, can react with biological nucleophiles. Due to their high reactivity and dense functionality, total syntheses of these molecules require strict control of the inherent reactivity and the appropriate design of synthetic intermediates. This review focuses on the recent total syntheses of some highly oxidized γ-lactam-containing natural products, including fused bicyclic (epolactaene, NG-391, lucilactaene, L-755,807), spirocyclic (azaspirene, pseurotin A, E, and F2, cephalimysin A-C, FD-838, and berkeleyamide D), and tricyclic (rubrobramide and talaramide A) skeletons, and on the structure-activity relationship studies of related molecules.

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Asymmetric Total Synthesis of Pseurotin A

Cited by 53 publications

References 25 publications

Assignment of the CD Cotton Effect to the Chiral Center in Pseurotins, and the Stereochemical Revision of Pseurotin A2

Assignment of the CD Cotton Effect to the Chiral Center in Pseurotins, and the Stereochemical Revision of Pseurotin A2

Synthesis of 3(2H)‐Furanones: A Review

Highly Oxidized γ-Lactam-Containing Natural Products: Total Synthesis and Biological Evaluation

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