Aphidicolin synthetic studies: a stereocontrolled end game

Rizzo, Carmelo J.; Smith, Amos B.

doi:10.1039/p19910000969

Cited by 21 publications

(11 citation statements)

References 44 publications

(7 reference statements)

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“…Both syntheses had as a target compound 5a, the acetonide of the periodic acid cleavage product of (+)-1, reconverted, though not diastereoselectively into (+)-1 [2]. This synthetic problem was overcome in 1988 when a solution to it was described [9,10]. Later syntheses of (±)-1 via 5a and 5b ( Figure 2) were published also by other groups [11][12][13][14][15][16][17][18][19].…”

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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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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“…) is a diterpenoid metabolite produced by different fungi including Cephalosporium aphidicola , N. sphaerica , and Harziella entomophilla . Its structure was determined using chemical and spectroscopic data and later confirmed by its stereocontrolled synthesis . Recently, aphidicolin was also isolated from Phoma sp.…”

Section: Fungal Metabolites and Their Synthetic Analogues In Cancer Cmentioning

confidence: 99%

Toward a Cancer Drug of Fungal Origin

Kornienko

Evidente²,

Vurro

et al. 2015

Medicinal Research Reviews

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Although fungi produce highly structurally diverse metabolites, many of which have served as excellent sources of pharmaceuticals, no fungi-derived agent has been approved as a cancer drug so far. This is despite a tremendous amount of research being aimed at the identification of fungal metabolites with promising anticancer activities. This review discusses the results of clinical testing of fungal metabolites and their synthetic derivatives, with the goal to evaluate how far we are from an approved cancer drug of fungal origin. Also, because in vivo studies in animal models are predictive of the efficacy and toxicity of a given compound in a clinical situation, literature describing animal cancer testing of compounds of fungal origin is reviewed as well. Agents showing the potential to advance to clinical trials are also identified. Finally, the technological challenges involved in the exploitation of fungal biodiversity and procurement of sufficient quantities of clinical candidates are discussed and potential solutions that could be pursued by researchers are highlighted.

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“…This problem was first tackled by Smith jr et al [25,26]. This problem was first tackled by Smith jr et al [25,26].…”

Section: Synthesismentioning

confidence: 99%

The Chemistry of Bioactive Diterpenes

Banerjee¹,

Laya²,

Mora³

et al. 2008

COC

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This article reviews the isolation, biological activity and syntheses of several diterpenes. The chemistry and biological activities of norditerpene dilactones have been described. The aim of the present article is to provide an overview on the important role of diterpenoid compounds in medicine and agriculture. The synthetic discussions of these diterpenes are very briefly described. Dedicated to Professor Kenji Mori for his valuable contributions to Terpene Chemistry.COOH Me Me OH Me Me H The Chemistry of Bioactive Diterpenes

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Aphidicolin synthetic studies: a stereocontrolled end game

Cited by 21 publications

References 44 publications

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

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

Toward a Cancer Drug of Fungal Origin

The Chemistry of Bioactive Diterpenes

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