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  A New Method for the Preparation of Non-Terminal Alkynes: Application to the Total Syntheses of Tulearin A and C

Lehr, K., Schulthoff, S., Ueda, Y., Mariz, R., Leseurre, L., Gabor, B., et al. (2015). A New Method for the Preparation of Non-Terminal Alkynes: Application to the Total Syntheses of Tulearin A and C. Chemistry – A European Journal, 21(1), 219-227. doi:10.1002/chem.201404873.

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chem_201404873_sm_miscellaneous_information.pdf (Supplementary material), 12MB
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chem_201404873_sm_miscellaneous_information.pdf
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Supporting Information
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Copyright Date:
2014
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Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim
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 Creators:
Lehr, Konrad1, Author           
Schulthoff, Saskia1, Author           
Ueda, Yoshihiro1, Author           
Mariz, Ronaldo1, Author           
Leseurre, Lucie1, Author           
Gabor, Barbara2, Author           
Fürstner, Alois1, Author           
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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Free keywords: alkynes; hydrosilylation; iron catalysis; metathesis; molybdenum; natural products
 Abstract: Lactones are known to react with the reagent generated in situ from CCl4 and PPh3 in a Wittig-type fashion to give gem-dichloro-olefin derivatives. Such compounds are now shown to undergo reductive alkylation on treatment with organolithium reagents RLi to furnish acetylene derivatives bearing the substituent R at their termini (R=Me, n-, sec-, tert-alkyl, silyl); the reaction can be catalyzed with either Cu(acac)2 or Fe(acac)3/1,2-diaminobenzene. Two alkynol derivatives prepared in this way from readily accessible lactone precursors served as the key building blocks for the total syntheses of the cytotoxic marine macrolides tulearin A (1) and C (2). The assembly of these fragile targets hinged upon ring closing alkyne metathesis (RCAM) followed by a formal trans-reduction of the resulting cycloalkynes via trans-hydrosilylation/protodesilylation.

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Language(s): eng - English
 Dates: 2014-08-152014-11-032015-01-02
 Publication Status: Published in print
 Pages: 9
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/chem.201404873
 Degree: -

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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim, Germany : VCH Verlagsgesellschaft
Pages: 9 Volume / Issue: 21 (1) Sequence Number: - Start / End Page: 219 - 227 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058