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Issue 66, 2015
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Total synthesis and stereochemical assignment of cryptolatifolione

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Abstract

An enantioselective total synthesis of cryptolatifolione and its C-8 epimer is presented in a protecting-group-free fashion. The synthesis relied on the use of a catalytic double Krische allylation, catalytic olefin metathesis and a C–H oxidation. Comparison of spectroscopic data of the synthetic isomers and natural product made possible the unambiguous elucidation of the absolute configuration of cryptolatifolione.

Graphical abstract: Total synthesis and stereochemical assignment of cryptolatifolione

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Publication details

The article was received on 16 May 2015, accepted on 10 Jun 2015 and first published on 10 Jun 2015


Article type: Paper
DOI: 10.1039/C5RA09186A
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RSC Adv., 2015,5, 53471-53476

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    Total synthesis and stereochemical assignment of cryptolatifolione

    L. F. T. Novaes, A. M. Sarotti and R. A. Pilli, RSC Adv., 2015, 5, 53471
    DOI: 10.1039/C5RA09186A

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