Asteriscanolide. A sesquiterpene lactone with a new natural skeleton.

Feliciano, Arturo San; Barrero, Alejandro F.; Medarde, Manuel; Corral, José M. Miguel del; Aramburu, A.; Perales, A.; Fayos, J.

doi:10.1016/s0040-4039(00)95101-3

Cited by 65 publications

(49 citation statements)

References 5 publications

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“…13 −15 In order to examine the chemical diversity and the structural variation of soft coral species inhabiting different geographic locations, we collected the specimen Sinularia capillosa from the coral reef near Hainan Island. Chromatographic (HPLC) and 1 H NMR spectroscopic analyses revealed that the EtOAc extract of this specimen featured numerous terpenoids, differing from those reported in the literature. 16−19 This paper reports the structure elucidation of the new asteriscane-type sesquiterpenoids 1−18.…”

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confidence: 77%

Asteriscane-Type Sesquiterpenoids from the Soft Coral Sinularia capillosa

Chen

Liu

et al. 2013

J. Nat. Prod.

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Chemical examination of the soft coral Sinularia capillosa collected from the South China Sea resulted in the isolation of 14 new asteriscane-type sesquiterpenoids, namely, capillosananes A-N (1-14), four new seco-asteriscanes, capillosananes O-R (15-18), and (-)-sinularone A and sinularone A. Their structures were determined on the basis of extensive spectroscopic analyses, while the absolute configurations were determined by CD and ECD calculation, Mosher's method, and chemical conversion. This is the first report of asteriscane-type sesquiterpenoids from soft corals, and capillosananes Q (17) and R (18) represent new seco-asteriscane skeletons. Capillosanane A exhibited potent antifouling activity against Balanus amphitrite, with an IC₅₀ value of 9.70 μM, while capillosananes B and I and (-)-sinularone A inhibited inflammation-related TNF-α in vitro.

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confidence: 77%

Asteriscane-Type Sesquiterpenoids from the Soft Coral Sinularia capillosa

Chen

Liu

et al. 2013

J. Nat. Prod.

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“…Since the discovery of (+)‐asteriscanolide ( 1 ) in 1985,5a it has captured the attention of the organic chemical community because of its unique structure; its challenging sesquiterpenoid framework contains an uncommon [6.3.0] carbocyclic system bridged by a butyrolactone fragment and five cis stereocenters. There have only been a few successful total syntheses of (+)‐asteriscanolide reported to date,6, 7 although a considerable amount of effort has been devoted to it 8.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of (+)‐Asteriscanolide: Further Exploration of the Rhodium(I)‐Catalyzed [(5+2)+1] Reaction of Ene‐Vinylcyclopropanes and CO

Liang

Jiang

Xiao-yue

et al. 2011

Chemistry An Asian Journal

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The total synthesis of (+)-asteriscanolide is reported. The synthetic route features two key reactions: 1) the rhodium(I)-catalyzed [(5+2)+1] cycloaddition of a chiral ene-vinylcyclopropane (ene-VCP) substrate to construct the [6.3.0] carbocyclic core with excellent asymmetric induction, and 2) an alkoxycarbonyl-radical cyclization that builds the bridging butyrolactone ring with high efficiency. Other features of this synthetic route include the catalytic asymmetric alkynylation of an aldehyde to synthesize the chiral ene-VCP substrate, a highly regioselective conversion of the [(5+2)+1] cycloadduct into its enol triflate, and the inversion of the inside-outside tricycle to the outside-outside structure by an ester-reduction/elimination to enol-ether/hydrogenation procedure. In addition, density functional theory (DFT) rationalization of the chiral induction of the [(5+2)+1] reaction and the diastereoselectivity of the radical annulation has been presented. Equally important is that we have also developed other routes to synthesize asteriscanolide using the rhodium(I)-catalyzed [(5+2)+1] cycloaddition as the key step. Even though these routes failed to achieve the total synthesis, these experiments gave further useful information about the scope of the [(5+2)+1] reaction and paved the way for its future application in synthesis.

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“…Asteriscunolides A–D and 6,7,9,10‐tetrahydroasteriscunolide contain a synthetically challenging 11‐membered ring, together with a bridged cyclic butenolide moiety (Figure ). Asteriscanolide, 6,7,9,10‐tetradehydroasteriscanolide, naupliolide and aquatolide have a rather unusual bicyclo[6.3.0]undecane core, as well as an adjoining butyrolactone moiety . A recent article reported several new members of the humulanolide family, namely 6β,7β‐epoxyasteriscunolide A, 2α,3α‐epoxyasteriscunolide C and asteriscanolidenol, which exhibited good bioactivity towards several human leukemia cancer cell lines …”

Section: Introductionmentioning

confidence: 99%

Ruthenium-Catalyzed Metathesis Cascade Reactions in Natural Products Synthesis

Han

2016

Chem. Rec.

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In this account, we provide a brief summary of recent developments in ruthenium-catalyzed metathesis cascade reactions towards the total synthesis of natural products. We also highlight recent progress from our own laboratory regarding the synthesis of securinega alkaloids and humulanolides, which has resulted in the development of novel ruthenium-catalyzed metathesis cascade reactions. Inspired and guided by the pioneering and elegant research conducted in this area, we developed a regio-controlled relay dienyne metathesis cascade reaction and a cyclobutene-promoted RCM/ROM/RCM cascade reaction for the synthesis of securinega alkaloids and humulanolides, respectively.

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Asteriscanolide. A sesquiterpene lactone with a new natural skeleton.

Cited by 65 publications

References 5 publications

Asteriscane-Type Sesquiterpenoids from the Soft Coral Sinularia capillosa

Asteriscane-Type Sesquiterpenoids from the Soft Coral Sinularia capillosa

Total Synthesis of (+)‐Asteriscanolide: Further Exploration of the Rhodium(I)‐Catalyzed [(5+2)+1] Reaction of Ene‐Vinylcyclopropanes and CO

Ruthenium-Catalyzed Metathesis Cascade Reactions in Natural Products Synthesis

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