Diastereocontrol in the Synthesis of Models of Rings C and D of Phorbol: Directing Effect of an Ether Substituent on Lithium Carbenoid Mediated Cyclopropanation

Drew, Michael G. B.; Harwood, Laurence M.; Macı́as-Sánchez, Antonio J.; Scott, Richard W.; Thomas, R. M.; Uguen, D.

doi:10.1002/1521-3757(20010618)113:12<2373::aid-ange2373>3.0.co;2-5

Angew. Chem.

2001

DOI: 10.1002/1521-3757(20010618)113:12<2373::aid-ange2373>3.0.co;2-5

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Diastereocontrol in the Synthesis of Models of Rings C and D of Phorbol: Directing Effect of an Ether Substituent on Lithium Carbenoid Mediated Cyclopropanation

Michael G. B. Drew

Laurence M. Harwood

Antonio J. Macı́as-Sánchez

et al.

Abstract: Komplementäre Diastereoselektivität wurde mit Dihalogen‐ und Dialkylcarbenen bei der Cyclopropanierung von 1 beobachtet (Weg a bzw. b). Die Umwandlung von 1 in 7,7‐Dimethylbicyclo[4.1.0]heptan‐1,2‐diole (±)‐2 und (±)‐3 ist der entscheidende Schritt der hier vorgestellten Strategie, die auf die Synthese von Phorbolderivaten abzielt. TBDMS=tert‐Butyldimethylsilyl.

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Cited by 10 publications

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References 24 publications

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“…We planned to perform enol ether formation via the respective dimethyl acetal and subsequent treatment with LDA under kinetic conditions . Instead of acetal formation, both diastereomers were converted directly into their respective enol ethers in the presence of (±)-CSA and HC(OMe) 3 in methanol.…”

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confidence: 99%

The Total Synthesis of Hyperfirin via a Cyclooctadiene Strategy

König,

Morgenstern,

Jauch

2024

Org. Lett.

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Polycyclic polyprenylated acylphloroglucinols (PPAPs) combine compelling structural complexity with effective biological activity. The total synthesis of Hyperfirin is reported as one linear sequence. Key to this novel modular strategy is to access the bicyclo[3.3.1]nonane-2,4,9-trione framework via transannular acylation of a decorated eight-membered ring, followed by late stage bridgehead substitution. The described route adds flexibility to PPAP construction and broadens the scope of eight-membered ring chemistry. * sı Supporting InformationThe Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.4c01836.Experimental details, characterization data for all new compounds, 1 H and 13 C NMR spectra, and X-ray data information (PDF) FAIR data, including the primary NMR FID files, for compounds 1, 11a,[13][14][15][16]19,[21][22][23][24][25] and 27 (ZIP) Accession Codes CCDC 2353409−2353411 and 2353415 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk

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confidence: 99%

The Total Synthesis of Hyperfirin via a Cyclooctadiene Strategy

König,

Morgenstern,

Jauch

2024

Org. Lett.

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Total Synthesis of (−)‐Jiadifenin

Yang

Chen

et al. 2012

Angewandte Chemie

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Das ABCD der Ringe: (−)‐Jiadifenin wurde in achtzehn Schritten ausgehend von 1‐[(E)‐(4′‐Brom‐2′‐butenyl)oxy]‐4‐methoxybenzol synthetisiert. Schlüsselschritte waren 1) eine Ireland‐Claisen‐Umlagerung zu Bildung der quartären Zentren C5 und C6, 2) eine intramolekulare Pauson‐Khand‐Reaktion (IMPKR), um die Ringe A und B zu erzeugen, und 3) eine [2+2]‐Photocycloaddition, die das ausschließlich kohlenstoffsubstituierte quartäre Zentrum C9 einführt.

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Total Synthesis of Diterpenoid Steenkrotin A

et al. 2015

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Aconcise and diastereoselective total synthesis of the diterpenoid (AE)-steenkrotin Ai sd escribed for the first time. The strategy mainly features three key ring formations:1 )a rhodium-catalyzed OÀHb ond insertion followed by an intramolecular carbonyl-ene reaction to build up the tetrahydrofuran subunit;2 )sequential SmI 2 -mediated Ueno-Stork and ketyl-olefin cyclizations to construct the [5,7] spirobicyclic skeleton;a nd 3) an intramolecular aldol condensation/vinylogous retro-aldol/aldol sequence to form the final six-membered ring with inversion of the relative configuration at the C7 position.

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Diastereocontrol in the Synthesis of Models of Rings C and D of Phorbol: Directing Effect of an Ether Substituent on Lithium Carbenoid Mediated Cyclopropanation

Cited by 10 publications

References 24 publications

The Total Synthesis of Hyperfirin via a Cyclooctadiene Strategy

The Total Synthesis of Hyperfirin via a Cyclooctadiene Strategy

Total Synthesis of (−)‐Jiadifenin

Total Synthesis of Diterpenoid Steenkrotin A

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