Total synthesis of talatisamine, a delphinine type alkaloid

The most abundant readily isolated alkaloids of the aerial portion of Aconitumcolumbianum Nutt• were found to be talatisamine and cammaconine. New spectral data for known derivatives of these alkaloids and descriptions of new derivatives are presented. Less abundant alkaloids identified included the known ones sachaconitine, talatizidine, isotalatizidine, and 14-O-acetyltalatisamine, and the new ones 8-O-methyltalatisamine and a tetrahydroxymonomethoxy alkaloid, columbianine, with the same oxygenation pattern and stereochemistry as cammaconine.

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“…The structure and stereochemistry of this alkaloid has been confirmed by total synthesis by Wiesner et a/. (6). 'Issued as NRCC No.…”

mentioning

confidence: 71%

Alkaloids of Aconitumcolumbianum Nutt_•

Boido¹,

Edwards²,

Handa³

et al. 1984

Can. J. Chem.

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“…The residue was distributed between water and dichloromethane. The organic layers gave 204 mg of crude product which crystallized from acetone-hexane giving 183 mg (84%) of oxoaconosine (8) …”

Section: Ronconosinementioning

confidence: 99%

A partial synthesis of aconosine

Edwards¹,

Kolt²,

Purushothaman³

1983

Can. J. Chem.

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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 talatisamine, a delphinine type alkaloid

Cited by 86 publications

References 1 publication

Alkaloids of Aconitumcolumbianum Nutt_•

Alkaloids of Aconitumcolumbianum Nutt_•

A partial synthesis of aconosine

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

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Total synthesis of talatisamine, a delphinine type alkaloid

Cited by 86 publications

References 1 publication

Alkaloids of Aconitumcolumbianum Nutt•

Alkaloids of Aconitumcolumbianum Nutt•

A partial synthesis of aconosine

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

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Product

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Alkaloids of Aconitumcolumbianum Nutt_•

Alkaloids of Aconitumcolumbianum Nutt_•