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A simple approach to the construction of the core structure present in bielschowskysin and hippolachnin A

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Abstract

A convenient route for the synthesis of oxacyclobutapentalene, the tricyclic bridged core structure present in bioactive marine diterpene bielschowskysin and the polyketide hippolachnin A, is reported. The key steps involve ring closing metathesis of a triene derived from D-mannitol to produce selectively the dihydrofuran derivative instead of the cyclopentene derivative and a Cu(I)-catalyzed intramolecular [2+2] photocycloaddition of the dihydrofuran derivative.

Synthesis of oxacyclobutapentalene, the core structure of bielschowskysin and hippolachnin A, has been achieved through ring closing metathesis and Cu(I)-catalysed intramolecular [2+2] photocycloaddition as the key steps.

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Acknowledgements

We are grateful to Department of Science and Technology, Government of India for financial support through J. C. Bose National Fellowship (SR/S-2/JCB-83/2011) awarded to SG. RD thanks Council of Scientific and Industrial Research, New Delhi for a research fellowship.

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Authors and Affiliations

  1. Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata, 700 032, India

    RITABRATA DATTA, MALASALA SUMALATHA & SUBRATA GHOSH

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  1. RITABRATA DATTA
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  2. MALASALA SUMALATHA
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Correspondence to SUBRATA GHOSH.

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Supplementary Information (SI)

All additional information regarding characterisation of the new compounds using 1H NMR, 13C NMR and 2D NMR spectra are given in the supplementary information, available at www.ias.ac.in/chemsci.

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DATTA, R., SUMALATHA, M. & GHOSH, S. A simple approach to the construction of the core structure present in bielschowskysin and hippolachnin A. J Chem Sci 128, 1019–1023 (2016). https://doi.org/10.1007/s12039-016-1109-x

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