Total Synthesis of Alotaketal A

Xuan, Mengyang; Paterson, Ian; Dalby, Stephen M.

doi:10.1021/ol302570k

Cited by 39 publications

(24 citation statements)

References 30 publications

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“…A recent study has shown that simple semisynthetic modification of natural ingenol esters enhanced their LRA potency and reduced their toxicity, demonstrating that SAR-driven improvement in therapeutic index is possible in these terpenoid families . Two total syntheses of alotaketal A have been reported, which provide access to this scaffold and analogues for SAR. , Therefore, the Phorbas sesterterpenoids 2 , 3 , 8 , and 14 reported herein represent a new set of terpenoid scaffolds that are interesting lead structures for SAR-driven development of LRA cell biology tools and drug candidates.…”

Section: Discussionmentioning

confidence: 99%

Sesterterpenoids Isolated from the Sponge Phorbas sp. Activate Latent HIV-1 Provirus Expression

et al. 2016

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Eight new sesterterpenoids, alotaketals D (8) and E (9), ansellones D (10), E (11), F (12), and G (13), and anvilones A (14) and B (15), have been isolated from extracts of the marine sponge Phorbas sp. collected in Howe Sound British Columbia, and their structures have been elucidated by analysis of NMR and MS data. Ansellone F (12) contains a rare 1,2-3,4-bis-epoxydecalin substructure. Anvilones A (14) and B (15) have an unprecedented tetracylic anvilane terpenoid carbon skeleton. Using a cell culture model of latent HIV-1 infection, ansellone A (3), alotaketal D (8), and anvilone A (14) were found to induce HIV proviral gene expression similar to the control compound prostratin (1), while the known sesterterpenoid alotaketal C (2), isolated from the same extract, was more potent and gave a stronger response than prostratin (1). Like prostratin (1), all of the Phorbas sesterterpenoids with latency reversal agent properties appear to activate protein kinase C signaling.

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Section: Discussionmentioning

confidence: 99%

Sesterterpenoids Isolated from the Sponge Phorbas sp. Activate Latent HIV-1 Provirus Expression

et al. 2016

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“…716 by two independent groups have conrmed the absolute conguration. 717,718 Four sesterterpenoids, phorone A 855, isophorbasone A 856, ansellone B 857 and phorbasone A acetate 858, were isolated from a S. Korean Phorbas sp. Compounds 857 and 858, described in the paper's supporting information, were low mM inhibitors of NO production in LPS-stimulated RAW 264.7 cells, while 855 and 856 are the rst examples of two new carbon skeletons.…”

Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2014

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This review covers the literature published in 2012 for marine natural products, with 1035 citations (673 for the period January to December 2012) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1241 for 2012), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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“…The potent and wide array of biological activities of alotaketals and phorbaketals have attracted considerable synthetic interest. The groups of Yang, and Dalby accomplished the elegant total synthesis of 1 by similar strategies, which involved late‐stage construction of the C ring through a Barbier‐type reaction and spiroketalization. Recently, the groups of Brimble and Bray disclosed two efficient strategies for the tricyclic spiroketal core, which unfortunately could not be elaborated to the natural products.…”

Section: Figurementioning

confidence: 99%

Unified Asymmetric Total Syntheses of (−)‐Alotaketals A–D and (−)‐Phorbaketal A

et al. 2017

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The novel tricyclic spiroketal alotane-type sesterterpenoids showed strikingly different biological activities and potency with subtle structural alterations. Asymmetric total syntheses of the tricyclic sesterterpenoids (-)-alotaketals A-D and (-)-phorbaketal A were accomplished [29-31 steps from (-)-malic acid] in a collective way for the first time. The key features of the strategy included 1) a new cascade cyclization of vinyl epoxy δ-keto-alcohols to forge the common tricyclic spiroketal intermediate, 2) a late-stage allylic C-H oxidation, and 3) olefin cross-metathesis to install the different side chains.

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Total Synthesis of Alotaketal A

Cited by 39 publications

References 30 publications

Sesterterpenoids Isolated from the Sponge Phorbas sp. Activate Latent HIV-1 Provirus Expression

Sesterterpenoids Isolated from the Sponge Phorbas sp. Activate Latent HIV-1 Provirus Expression

Marine natural products

Unified Asymmetric Total Syntheses of (−)‐Alotaketals A–D and (−)‐Phorbaketal A

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