Carbon—Carbon Alkylations of Enamines with Mannich Bases

Strandtmann, M. Von; Cohen, M. P.; Shavel, John

doi:10.1021/jo01020a530

Cited by 24 publications

(14 citation statements)

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“…Cyclohexanone derivative 37 , a desulfenated analogue of compound 32 , is available from gramine ( 36 ) 36. It was a key intermediate in the synthesis of neocryptolepine reported by Walton's group (Scheme ) 37…”

Section: Total Syntheses Of Neocryptolepinementioning

confidence: 99%

“…Microwave irradiation of 38 in t BuPh afforded a 69 % yield of tricyclic derivative 40 , through the intermediacy of 39 . In turn, 40 underwent a second in situ dehydrogenation step, resulting in aromatization of the newly formed pyridine ring to provide 34 , formally affording a total synthesis of neocryptolepine in five steps from 36 36…”

Section: Total Syntheses Of Neocryptolepinementioning

confidence: 99%

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Understanding Bacterial Bioluminescence: A Theoretical Study of the Entire Process, from Reduced Flavin to Light Emission

Cong

Liu

Ferré

et al. 2014

Chemistry A European J

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Bacterial bioluminescence (BL) has been successfully applied in water-quality monitoring and in vivo imaging. The attention of researchers has been attracted for several decades, but the mechanism of bacterial BL is still largely unknown due to the complexity of the multistep reaction process. Debates mainly focus on three key questions: How is the bioluminophore produced? What is the exact chemical form of the bioluminophore? How does the protein environment affect the light emission? Using quantum mechanics (QM), combined QM and molecular mechanics (QM/MM) and molecular dynamic (MD) calculations in gas-phase, solvent and protein environments, the entire process of bacterial BL was investigated, from flavin reduction to light emission. This investigation revealed that: 1) the chemiluminescent decomposition of flavin peroxyhemiacetal does not occur through the intramolecular chemical initiated electron exchange luminescence (CIEEL) or the "dioxirane" mechanism, as suggested in the literature. Instead, the decomposition occurs according to the charge-transfer initiated luminescence (CTIL) mechanism for the thermolysis of dioxetanone. 2) The first excited state of 4a-hydroxy-4a,5-dihydroFMN (HFOH) was affirmed to be the bioluminophore of bacterial BL. This study provides details regarding the mechanism by which bacterial BL is produced and is helpful in understanding bacterial BL in general.

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Section: Total Syntheses Of Neocryptolepinementioning

confidence: 99%

Section: Total Syntheses Of Neocryptolepinementioning

confidence: 99%

Understanding Bacterial Bioluminescence: A Theoretical Study of the Entire Process, from Reduced Flavin to Light Emission

Cong

Liu

Ferré

et al. 2014

Chemistry A European J

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“…3,3-Dimethyl-3H-naphtho[2,1-b]pyran (50) was first converted to its bromohydrin 51 followed by CrO 3 oxidation and subsequent reduction via Zn/AcOH to afford 3,3-dimethyl-2,3-dihydronaphtho[2,1-b]pyran-1-one (52). Application of potassium hydroxide on the bromohydrin 51 resulted in an epoxide intermediate (53), which was later converted to 3,3-dimethyl-2,3-dihydro-1H-naphtho[2,1-b]pyran-2-ol (54) [43].…”

Section: Methods Of Synthesis Of 23-dihydro-1h-naphtho[21-b]pyransmentioning

confidence: 99%

“…Strandtmann and his research group reported a new strategy to produce 3-morpholino-2,2-dimethyl-2,3-dihydro-1H-naphtho[2,1-b]pyran (62) from 2-naphthol Mannich bases (63) and an enamine (Scheme 25; yield not reported) [49,50]. The proposed mechanism involved elimination of the dimethylamine from the Mannich base followed by a Michael-type addition to the enamine.…”

Section: Methods Of Synthesis Of 23-dihydro-1h-naphtho[21-b]pyransmentioning

confidence: 99%

Synthetic approaches to 3H‐naphtho[2,1‐b]pyrans and 2,3‐dihydro‐1H‐naphtho[2,1‐b]pyrans

Jha

Huang

2009

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).Naphtho [2,1-b]pyran nuclei are prevalent in natural products with significant biological and medicinal properties. 3,3-Disubstituted 3H-naphtho[2,1-b]pyrans are photochromic and find use in electronic display systems, ophthalmic lenses, optical switches, and temporary or permanent memories. Of the various possible structural isomers of naphthopyran framework, this review is an account of reported synthetic procedures to produce 3H-naphtho[2,1-b]pyrans and their dihydro analogs, 2,3-dihydro-1H-naphtho[2,1-b]pyrans. The advantages and disadvantages of each procedure in terms of yields, complexity, formation of side-products, use of uncommon/expensive reagents, etc., are also described.

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“…Cyclohexanone derivative 37, a desulfenated analogue of compound 32, is available from gramine (36). [36] It was a key intermediate in the synthesis of neocryptolepine reported by Walton's group (Scheme 3). [37] Indolo ketone 37 was prepared in 78 % yield from the reaction between gramine and cyclohex-1-enylpyrrolidine, and the corresponding O-phenyl oxime ether 38 was then obtained in 70 % yield.…”

Section: Indoles As Starting Materialsmentioning

confidence: 99%

Neocryptolepine (Cryprotackieine), A Unique Bioactive Natural Product: Isolation, Synthesis, and Profile of Its Biological Activity

et al. 2014

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Carbon—Carbon Alkylations of Enamines with Mannich Bases

Cited by 24 publications

References 0 publications

Understanding Bacterial Bioluminescence: A Theoretical Study of the Entire Process, from Reduced Flavin to Light Emission

Understanding Bacterial Bioluminescence: A Theoretical Study of the Entire Process, from Reduced Flavin to Light Emission

Synthetic approaches to 3H‐naphtho[2,1‐b]pyrans and 2,3‐dihydro‐1H‐naphtho[2,1‐b]pyrans

Neocryptolepine (Cryprotackieine), A Unique Bioactive Natural Product: Isolation, Synthesis, and Profile of Its Biological Activity

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