A new synthesis of chasmanine and 13-desoxydelphonine: a preferred route to the aromatic intermediate

Tsai, T. Y. R.; Nambiar, Krishnan P.; Krikorian, Dikran; Botta, Maurizio; Marini-Bettolo, R.; Wiesner, K.

doi:10.1139/v79-341

Cited by 15 publications

(8 citation statements)

References 3 publications

(3 reference statements)

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“…The rearrangement reaction, a so-called Wagner–Meerwein rearrangement, has also been used for the chemical synthesis of aconitine-type diterpenoid alkaloids (Scheme ). Wiesner and co-workers employed a tosylate or a bromide as a substrate for the Wagner–Meerwein rearrangement, leading to the syntheses of talatisamine ( 3 ), chasmanine ( 4 ), and 13-desoxydelphonine . Sarpong and co-workers recently reported concise total syntheses of weisaconitine D ( 5 ) and liljestrandinine using the rearrangement reactions of triflates .…”

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confidence: 99%

Synthesis of Cardiopetaline via a Wagner–Meerwein Rearrangement without Preactivation of the Pivotal Hydroxy Group

2017

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A synthesis of cardiopetaline has been accomplished via a Wagner-Meerwein rearrangement of a diol having the denudatine skeleton. The Wagner-Meerwein rearrangement could be facilitated simply by heating the diol with p-toluenesulfonic acid in pivalic acid, without preactivating the pivotal hydroxy group. This strategy does not require differentiation of several hydroxy groups in the substrate for the Wagner-Meerwein rearrangement and could be applied to the synthesis of more highly oxygenated aconitine-type diterpenoid alkaloids.

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confidence: 99%

Synthesis of Cardiopetaline via a Wagner–Meerwein Rearrangement without Preactivation of the Pivotal Hydroxy Group

2017

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“…This choice would permit adoption of (+)-podocarpic acid (4) as starting material. [24][25][26]. The end of this fruitful and exciting experience coincided with the disclosure of the first two syntheses of (±)-aphidicolin (1) [7,8].…”

Section: Synthesis Of 17-noraphidicolan-16-one and 17-norstemodamentioning

confidence: 87%

“…Between 1976 and 1978 one of us (RMB) had been involved, as a member of the Wiesner group at the University of New Brunswick (Fredericton, NB, Canada), in the synthesis of some diterpene alkaloids whose C/D ring system, constituted by a bicyclo [ [24][25][26]. The end of this fruitful and exciting experience coincided with the disclosure of the first two syntheses of (±)-aphidicolin (1) [7,8].…”

Section: Synthesis Of 17-noraphidicolan-16-one and 17-norstemodamentioning

confidence: 99%

(+)-Podocarpic Acid as Chiral Template in the Synthesis of Aphidicolane, Stemodane and Stemarane Diterpenoids †

et al. 2016

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Abstract:In this review the synthetic work in the field of aphidicolane, stemodane and stemarane diterpenoids, in which readily available (+)-podocarpic acid (4) was used as chiral template for the construction of their polycyclic structures, is described as it developed along the years. In the frame of this work (+)-podocarpic acid (4) was a very useful tool in a model study leading to the syntheses of tetracyclic ketones 7 and 8, models of key intermediates 5a and 6 in the syntheses of (+)-aphidicolin (1) and (+)-stemodin (2a), respectively. (+)-Podocarpic acid (4) was also converted into (+)-2-deoxystemodinone (2d), allowing confirmation of the stemodane diterpenoids absolute configuration, into (+)-aphidicol-15-ene (36) and into Stemodia chilensis tetracyclic diterpenoid (+)-19-acetoxystemodan-12-ol (2f), allowing confirmation of its structure. (+)-Podocarpic acid (4) was then extensively used in the work which led to the synthesis of (+)-stemar-13-ene (57) and (+)-18-deoxystemarin (3b). Finally, (+)-4 was converted into (+)-2-deoxyoryzalexin S (66), which made it possible to demonstrate that the structure of (+)-66 could not be attributed to a Chilean Calceolaria isolated diterpenoid to which this structure had been assigned.

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“…Kelly and co-workers at the University of New Brunswick (St. John N.B., Canada) and our group, both belonging to the Wiesner [46] school, got engaged with the synthesis of these very interesting compounds by the approach had been developed by their Mentor for the construction of the C/D ring system of diterpene alkaloids [47,48,49,50,51,52,53].…”

Section: Synthesismentioning

confidence: 99%

Stemarane Diterpenes and Diterpenoids

Leonelli

Valletta

Migneco

et al. 2019

IJMS

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In this article the scientific activity carried out on stemarane diterpenes and diterpenoids, isolated over the world from various natural sources, was reviewed. The structure elucidation of stemarane diterpenes and diterpenoids was reported, in addition to their biogenesis and biosynthesis. Stemarane diterpenes and diterpenoids biotransformations and biological activity was also taken into account. Finally the work leading to the synthesis and enantiosynthesis of stemarane diterpenes and diterpenoids was described.

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A new synthesis of chasmanine and 13-desoxydelphonine: a preferred route to the aromatic intermediate

Abstract: An efficient synthesis (stereo- and regiospecific) of compound I (Scheme I) from o-cresol is described.

Cited by 15 publications

References 3 publications

Synthesis of Cardiopetaline via a Wagner–Meerwein Rearrangement without Preactivation of the Pivotal Hydroxy Group

Synthesis of Cardiopetaline via a Wagner–Meerwein Rearrangement without Preactivation of the Pivotal Hydroxy Group

(+)-Podocarpic Acid as Chiral Template in the Synthesis of Aphidicolane, Stemodane and Stemarane Diterpenoids †

Stemarane Diterpenes and Diterpenoids

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