13-Step total synthesis of Dendrodolide K following iterative Bartlett–Smith iodocarbonate cyclization

Mohapatra, Debendra K.; Karthik, P.; Gajula, Srinivas; Yadav, J. S.

doi:10.1016/j.tetlet.2015.09.126

Cited by 10 publications

(5 citation statements)

References 49 publications

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“…From the retrosynthetic perspective, we envisioned that the disconnection of peniciketals at the featured bicyclo[3.3.1] nonane core presented the possibility of the late-stage photochemical union to unite the northern and southern hemispheres ( 13 and 14 , respectively, Scheme ). The [6,6]-spiroketal 14 would be assembled by a Type I ARC tactic from commercially available linchpin 15 and two different electrophiles 16 and (+)- 17 …”

Section: Resultsmentioning

confidence: 99%

Total Syntheses of (+)-Peniciketals A-B and (−)-Diocollettines A Exploiting a Photoisomerization/Cyclization Union Protocol

et al. 2021

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A late-stage photoisomerization/cyclization union tactic, in conjunction with Type I Anion Relay Chemistry (ARC), permits enantioselective total syntheses and then biological evaluation of (+)-peniciketals A and B. The photochemical protocol was further showcased by an efficient three-step construction of the architecturally complex polycyclic skeleton found in (−)-diocollettines A. The mechanism and diastereoselectivity of the photochemical protocol have also been explored by both experiment and density functional theory calculations.

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Section: Resultsmentioning

confidence: 99%

Total Syntheses of (+)-Peniciketals A-B and (−)-Diocollettines A Exploiting a Photoisomerization/Cyclization Union Protocol

et al. 2021

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“…336 Total synthesis of the macrolide dendrodolide K 337 (Dendrodochium sp.) has been accomplished from a commercially available substrate by a convergent strategy 338 and other dendrolides (F, G, I, J and L 337 ) have also been synthesised via a unied strategy employing ring-closing metathesis. 339 A unied strategy was also employed in the total synthesis of luteoalbusins A and B, 340 indole diketopiperazines isolated from sediment-derived Acrostalagmus luteoalbus.…”

Section: Marine-sourced Fungi (Excluding From Mangroves)mentioning

confidence: 99%

Marine natural products

et al. 2017

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Covering: 2015. Previous review: Nat. Prod. Rep., 2016, 33, 382-431This review covers the literature published in 2015 for marine natural products (MNPs), with 1220 citations (792 for the period January to December 2015) 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 (1340 in 429 papers for 2015), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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“…derived from sea cucumber Holothuria nobilis Selenka in the South China Sea [ 143 ]. Dendrodolide K was obtained from a commercially available substrate by a convergent strategy, and the dendrolides F, G, I, J, and L were synthesized via a unified strategy employing ring-closing metathesis [ 144 , 145 ].…”

Section: Chemical and Biological Diversity Of Marine-derived Macrolidesmentioning

confidence: 99%

Marine-Derived Macrolides 1990–2020: An Overview of Chemical and Biological Diversity

et al. 2021

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Macrolides are a significant family of natural products with diverse structures and bioactivities. Considerable effort has been made in recent decades to isolate additional macrolides and characterize their chemical and bioactive properties. The majority of macrolides are obtained from marine organisms, including sponges, marine microorganisms and zooplankton, cnidarians, mollusks, red algae, bryozoans, and tunicates. Sponges, fungi and dinoflagellates are the main producers of macrolides. Marine macrolides possess a wide range of bioactive properties including cytotoxic, antibacterial, antifungal, antimitotic, antiviral, and other activities. Cytotoxicity is their most significant property, highlighting that marine macrolides still encompass many potential antitumor drug leads. This extensive review details the chemical and biological diversity of 505 macrolides derived from marine organisms which have been reported from 1990 to 2020.

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13-Step total synthesis of Dendrodolide K following iterative Bartlett–Smith iodocarbonate cyclization

Cited by 10 publications

References 49 publications

Total Syntheses of (+)-Peniciketals A-B and (−)-Diocollettines A Exploiting a Photoisomerization/Cyclization Union Protocol

Total Syntheses of (+)-Peniciketals A-B and (−)-Diocollettines A Exploiting a Photoisomerization/Cyclization Union Protocol

Marine natural products

Marine-Derived Macrolides 1990–2020: An Overview of Chemical and Biological Diversity

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