New avenues for the synthesis of ent-kaurene diterpenoids

Riehl, Paul S.; DePorre, Yvonne C.; Armaly, Ahlam M.; Groso, Emilia J.; Schindler, Corinna S.

doi:10.1016/j.tet.2015.04.116

Cited by 70 publications

(40 citation statements)

References 97 publications

(69 reference statements)

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“…4. Compounds 1 and 2 share a common precursor i, which undergoes a C13-alkyl shift to form a carbocation center at C-1618. The carbocation center at C-16 can then be attacked by H 2 O from two sites to form diastereomers 1 and 2 .…”

Section: Resultsmentioning

confidence: 99%

Rhodomollins A and B, two Diterpenoids with an Unprecedented Backbone from the Fruits of Rhododendron molle

Liu

Yan

et al. 2016

Sci Rep

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Two new grayanoids, rhodomollin A (1) and rhodomollin B (2), possessing an unprecedented D-homo grayanane carbon skeleton, were isolated from the fruits of Rhododendron molle. The structures of 1 and 2 were fully characterized using a combination of spectroscopic analyses and X-ray crystallography. Rhodomollin B (2) exhibited modest activity against influenza virus A/95-359, with an IC50 value of 19.24 μM.

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Section: Resultsmentioning

confidence: 99%

Rhodomollins A and B, two Diterpenoids with an Unprecedented Backbone from the Fruits of Rhododendron molle

Liu

Yan

et al. 2016

Sci Rep

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“…39 Maoecrystal Z is closely related to the 6,7- seco-ent -kauranoid natural products which includes maoecrystal-V and to which anticancer biological properties has been ascribed. 40 For the formation of the complex polycyclic core, the Reisman group employed a cyclization cascade which features tertiary radical ( 120 ) as a key intermediate. The authors propose that the aldehyde distal to the spirocycle is reduced first, perhaps due to its greater steric accessibility relative to the aldehyde adjacent to the geminal dimethyl group.…”

Section: Tertiary Radicals In Natural Product Synthesismentioning

confidence: 99%

Radicals in natural product synthesis

et al. 2018

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Free radical intermediates have intrigued chemists since their discovery, and an ever-increasing appreciation for their unique reactivity has resulted in the widespread utilization of these species throughout the field of chemical synthesis. This is most evident from the recent surge in the application of intermolecular radical reactions that feature in complex molecule syntheses. This tutorial review will discuss the diverse methods utilized for radical generation and reactivity to form critical bonds in natural product total synthesis. In particular, stabilized (e.g. benzyl) and persistent (e.g. TEMPO) radicals will be the primary focus.

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“…Chemical constituents and biological activities of Isodon plants have been the subjects of continuous studies for decades (Lazarski et al, 2014;Sun et al, 2006;Wang et al, 2011). ent-Kaurene diterpenoids are the major focus of the bioactive compounds in the genus (Lu et al, 2013;Riehl et al, 2015). In our recent studies, we have discovered several novel types of non-ent-kaurene diterpenes from the Isodon genus.…”

Section: Introductionmentioning

confidence: 98%

Isolation, evaluation of bioactivity and structure determination of amethinol A, a prototypic amethane diterpene from Isodon amethystoides bearing a six/five/seven-membered carbon-ring system

Zhao¹,

Sarwar²,

Ye³

et al. 2018

Acta Crystallogr C

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We report the isolation of a novel diterpene, designated as `amethane', from Isodon amethystoides (Lamiaceae). The diterpene [amethinol A; systematic name: (4aR,4bR,7R,10aS)-4b,7-dihydroxy-7-isopropyl-1,1-dimethyl-9-oxododecahydrobenzo[a]azulene-4a(2H)-carboxylic acid], possesses a unique skeleton containing a six/five/seven-membered tricyclic system. Intermolecular O-H...O close contacts were found to the carboxyl, carbonyl and hydroxy groups, connecting molecules into a two-dimensional structure. A possible biosynthetic pathway has been proposed. In addition, the compound was evaluated for its biological activities against different disease targets, and was found to significantly attenuate RORγt-dependent autoimmune responses.

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New avenues for the synthesis of ent-kaurene diterpenoids

Cited by 70 publications

References 97 publications

Rhodomollins A and B, two Diterpenoids with an Unprecedented Backbone from the Fruits of Rhododendron molle

Rhodomollins A and B, two Diterpenoids with an Unprecedented Backbone from the Fruits of Rhododendron molle

Radicals in natural product synthesis

Isolation, evaluation of bioactivity and structure determination of amethinol A, a prototypic amethane diterpene from Isodon amethystoides bearing a six/five/seven-membered carbon-ring system

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