Biomimetic Synthesis Enables the Structure Revision of Littordials E and F and Drychampone B

Castro, Tomás Vieira de; Yahiaoui, Oussama; Peralta, Ricardo A.; Fallon, Thomas; Lee, Victor; George, Jonathan H.

doi:10.1021/acs.orglett.0c03156

Cited by 19 publications

(10 citation statements)

References 44 publications

(24 reference statements)

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“…We therefore propose that the structure of anthopogochromane should be revised to 28 . This reassignment is also supported by the proposed biosynthesis of anthopogochromane via a stereoselective, intramolecular [2 + 2] cycloaddition of 27 .…”

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confidence: 61%

Biomimetic Total Synthesis of the Rubiginosin Meroterpenoids

et al. 2020

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Total synthesis of the Rhododendron meroterpenoids rubiginosins A and G, which both contain unusual 6−6−6−4 ring systems, has been achieved using a bioinspired cascade approach. Stepwise synthesis of these natural products, and the related 6−6−5−4 meroterpenoids fastinoid B and rhodonoid B, from naturally occurring chromene precursors is also reported.Rhododendron plants are a rich source of stereochemically complex, polycyclic meroterpenoids. Among the various possible scaffolds, the 6−6−6−4 ring system (Figure 1a) is

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confidence: 61%

Biomimetic Total Synthesis of the Rubiginosin Meroterpenoids

et al. 2020

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“…A related issue is that natural product structures are occasionally corrected due to re-isolation and re-evaluation ( 20 ), computational reassessment of the original NMR data ( 21–23 ), or total synthesis ( 24 , 25 ). The Natural Products Atlas includes fields and search terms for reassignment data; however, the reassignment dataset remains incomplete.…”

Section: Resultsmentioning

confidence: 99%

The Natural Products Atlas 2.0: a database of microbially-derived natural products

Santen

Poynton

Iskakova

et al. 2021

Nucleic Acids Research

167

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Within the natural products field there is an increasing emphasis on the study of compounds from microbial sources. This has been fuelled by interest in the central role that microorganisms play in mediating both interspecies interactions and host-microbe relationships. To support the study of natural products chemistry produced by microorganisms we released the Natural Products Atlas, a database of known microbial natural products structures, in 2019. This paper reports the release of a new version of the database which includes a full RESTful application programming interface (API), a new website framework, and an expanded database that includes 8128 new compounds, bringing the total to 32 552. In addition to these structural and content changes we have added full taxonomic descriptions for all microbial taxa and have added chemical ontology terms from both NP Classifier and ClassyFire. We have also performed manual curation to review all entries with incomplete configurational assignments and have integrated data from external resources, including CyanoMetDB. Finally, we have improved the user experience by updating the Overview dashboard and creating a dashboard for taxonomic origin. The database can be accessed via the new interactive website at https://www.npatlas.org.

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“…s, 1H), 1.34 (d, J = 9.8 Hz, 1H), 1.32-1.27 (m, 1H), 1.18 (s, 3H), 1.03 (s, 3H), 1.00 (s, 3H), 0.99 (s, 3H). 13 NO 5 388.2110). The structure was confirmed by single-crystal X-ray analysis.…”

Section: Crystal Structure Analysismentioning

confidence: 99%

“…(−)-β-Caryophyllene ((−)-1) can be obtained from different natural sources in large quantities and can be used not only as a cheap, renewable starting material to access more complex low-abundance natural compounds, but also to study biosynthetic connections in nature. Several natural product syntheses from (−)-β-caryophyllene have been recently demonstrated, including the biomimetic syntheses of meroterpenoids, [4][5][6][7][8] semisyntheses of rumphellaones A-C, 9 as well as the rearrangement of caryophyllene derivative to the tricyclic presilphiperfolan-1β-ol structure, 10 providing evidence for biosynthetic relationships in nature. Only few examples to date depict the applicability of β-caryophyllene and β-caryophyllene oxide in gramscale syntheses of natural products of rare occurrence.…”

Section: Introductionmentioning

confidence: 99%