Total synthesis of the calycanthaceous alkaloids

Hendrickson, James B.; Göschke, Richard; Rees, R. W.

doi:10.1016/s0040-4020(01)98619-3

Cited by 96 publications

(37 citation statements)

References 10 publications

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“…The potent antinociceptive activity of dimeric or polymeric pyrrolidinoindoline alkaloids that interact with opioid receptors was recently reported by Elisabetsky-Verotta's group. 51,52) The syntheses of these alkaloids have been accomplished so far by using the direct coupling reaction of tryptamine derivatives under various conditions [53][54][55][56][57] as well as by employing a multistep procedure via an elegant strategy. [58][59][60] Initially, we treated N b -carbomethoxytryptamine (67) with PIDA under the conditions developed above; however, this resulted mainly in the recovery of the starting material.…”

Section: Preparation Of Mitragynine Derivativesmentioning

confidence: 99%

“…Therefore, both alkaloids act on ileal smooth muscle, leading to the inhibition of the electrically induced twitch in guinea pig ileum preparation. The compounds (54)(55)(56) modifying the b-methoxyacrylate moiety in 1 exhibited very weak or no opioid agonistic activity, indicating that this function is essential for binding to the opioid receptors. The N b oxide derivative (53) showed no opioid agonistic activity in guinea pig ileum preparation.…”

Section: Pharmacological Evaluation Of Mitragynine Analogues For Opiomentioning

confidence: 99%

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Chemistry and Pharmacology of Analgesic Indole Alkaloids from the Rubiaceous Plant, Mitragyna speciosa

2004

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The leaves of a tropical plant, Mitragyna speciosa KORTH (Rubiaceae), have been traditionally used as a substitute for opium. Phytochemical studies of the constituents of the plant growing in Thailand and Malaysia have led to the isolation of several 9-methoxy-Corynanthe-type monoterpenoid indole alkaloids, including new natural products. The structures of the new compounds were elucidated by spectroscopic and/or synthetic methods. The potent opioid agonistic activities of mitragynine, the major constituent of this plant, and its analogues were found in in vitro and in vivo experiments and the mechanisms underlying the analgesic activity were clarified. The essential structural features of mitragynines, which differ from those of morphine and are responsible for the analgesic activity, were elucidated by pharmacological evaluation of the natural and synthetic derivatives. Among the mitragynine derivatives, 7-hydroxymitragynine, a minor constituent of M. speciosa, was found to exhibit potent antinociceptive activity in mice.

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Section: Preparation Of Mitragynine Derivativesmentioning

confidence: 99%

Section: Pharmacological Evaluation Of Mitragynine Analogues For Opiomentioning

confidence: 99%

Chemistry and Pharmacology of Analgesic Indole Alkaloids from the Rubiaceous Plant, Mitragyna speciosa

2004

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“…The X-ray of crystal structure was later reported by Fridrichsons et al [14]. The presence of two N-methyl groups and a significantly different specific rotation from that of chimonanthine (a dimeric compound which was also isolated from this plant), suggested hodgkinsine was a stereoisomer of chimonanthine [15]. Hodgkinsine is a potent analgesic, with results comparable to morphine in murine models using the hot-plate and tail-flick tests [16][17].…”

Section: Hodgkinsine (5)mentioning

confidence: 85%

Characterization Of Alkaloids From The Leaves Of Psychotria Malayana Jack Of Lombok Island On The Basis Of Gas Chromatography-Mass Spectroscopy

Hadi

Rahmawati

Asnawati

et al. 2014

J. Pure App. Chem. Res.

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The genus Psychotria is well known as a source of alkaloids and has contributed several novel indole-type alkaloids with quite a broad spectrum of bioactivities. This study was focused on identifying the alkaloids from the leaves of P. malayana Jack from Lombok island on the basis of Gas Chromatography-Mass Spectroscopy (GC-MS) data and the sample preparation followed acid-base extraction. The study showed that the major alkaloid contained by the leaves was hodgkinsine and other minor compounds, namely calycanthine, chimonantine, 2-ethyl-6-methylpyrazine, and 3-methyl-1,2,3,4-tetrahydrogamma-carboline. Bioactivities of the compounds were also discussed.

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“…As a consequence of this stability, under acidic conditions, (+)-calycanthine is readily formed from the isomeric 3a,3a'-connected bispyrrolidino [2,3-b]indoline, (À)-chimonanthine (5). [9][10][11] The facility with which this rearrangement takes place leaves unclear whether calycanthine is a genuine natural product or an isolation artifact. The structure of (À)-chimonanthine was settled in 1962 by single-crystal X-ray analysis of its dihydrobromide salt.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of Complex Cyclotryptamine Alkaloids: Stereocontrolled Construction of Quaternary Carbon Stereocenters

2007

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Our ability to access the more complex members of the cyclotryptamine family of alkaloids, and to exploit their disparate biological activities, is limited by the synthetic challenge posed by their oligomeric, polyindoline structures. A recurring structural theme within these molecules is the presence of multiple quaternary stereocenters in close proximity to one another. Over the last decade, we have developed a set of transformations that allow rapid access to polyindolines, a number of which exploit the ability of catalytic levels of palladium to orchestrate carbon-carbon bond formation with impressive levels of regio- and stereocontrol. This review tells the story behind the development of this toolbox of synthetic methods, and their validation through the total synthesis of a number of structurally complex cyclotryptamine alkaloids. It also highlights an aspect of asymmetric catalysis that has received little attention, the ability of catalytic asymmetric reactions to selectively elaborate complex, polyfunctional molecules.

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Total synthesis of the calycanthaceous alkaloids

Cited by 96 publications

References 10 publications

Chemistry and Pharmacology of Analgesic Indole Alkaloids from the Rubiaceous Plant, Mitragyna speciosa

Chemistry and Pharmacology of Analgesic Indole Alkaloids from the Rubiaceous Plant, Mitragyna speciosa

Characterization Of Alkaloids From The Leaves Of Psychotria Malayana Jack Of Lombok Island On The Basis Of Gas Chromatography-Mass Spectroscopy

Total Synthesis of Complex Cyclotryptamine Alkaloids: Stereocontrolled Construction of Quaternary Carbon Stereocenters

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