Total synthesis of delphinine-type alkaloids by simple, fourth generation methods

Wiesner, K.

doi:10.1351/pac197951040689

Cited by 65 publications

(14 citation statements)

References 8 publications

(14 reference statements)

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“…Owing to their architectural complexity and diversity, the chemical synthesis of diterpenoid alkaloids has attracted considerable attention . Whereas most synthetic endeavors targeted a specific structural type, the groups of Wiesner,, Sarpong, and Fukuyama completed the total synthesis of aconitine‐type diterpenoid alkaloids by critical Wagner–Meerwein‐type rearrangement reactions from the denudatine skeletons, as guided by the biosynthetic hypothesis. Furthermore, Baran and co‐workers reported an elegant approach to a hetidine core structure through a tandem condensation/azomethine ylide isomerization/Mannich cyclization sequence via a putative atisine intermediate .…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Atisine, Ajaconine, Denudatine, and Hetidine Diterpenoid Alkaloids by a Bioinspired Approach

Zhu

Wang

et al. 2016

Angew Chem Int Ed

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A unified approach to four different (atisine, ajaconine, denudatine, and hetidine) diterpenoid alkaloid skeletons was developed and applied to the total synthesis of the natural products dihydroajaconine (2, atisine type) and gymnandine (4, denudatine type). The synthesis features a biogenetically inspired strategy that relies on C-H oxidation, aza-pinacol coupling, and aza-Prins cyclization as key steps.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Atisine, Ajaconine, Denudatine, and Hetidine Diterpenoid Alkaloids by a Bioinspired Approach

Zhu

Wang

et al. 2016

Angew Chem Int Ed

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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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“…The end of this fruitful and exciting experience coincided with the disclosure of the first two syntheses of (±)-aphidicolin (1) [7,8]. Thus, back in Rome, we desired to show that the approach developed by Wiesner for the construction of the C/D ring system of diterpene alkaloids [27][28][29][30] could be also particularly convenient for the synthesis of the aphidicolane and stemodane systems. In fact the above rearrangement would have not only produced the required bicyclo[3.2.1]octane system but also introduced the oxygenated function present at C-16 in 5a and at C-13 in 6.…”

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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Total synthesis of delphinine-type alkaloids by simple, fourth generation methods

Abstract: A direct fully stereo-and regiospecific synthesis of crystalline racemic 13-desoxydelphonine from o-cresol is described.

Cited by 65 publications

References 8 publications

Synthesis of Atisine, Ajaconine, Denudatine, and Hetidine Diterpenoid Alkaloids by a Bioinspired Approach

Synthesis of Atisine, Ajaconine, Denudatine, and Hetidine Diterpenoid Alkaloids by a Bioinspired Approach

Stemarane Diterpenes and Diterpenoids

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

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