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Synlett 2009(1): 23-27  
DOI: 10.1055/s-0028-1087378
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Thieme Chemistry Journal Awardees - Where are They Now? Efforts towards the Total Synthesis of Vinigrol

Jason G. M. Morton, Laura D. Kwon, John D. Freeman, Jon T. Njardarson*
Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY 14853-1301, USA
Fax: +1(607)2554137; e-Mail: jn96@cornell.edu;
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Publikationsverlauf

Received 12 September 2008
Publikationsdatum:
12. Dezember 2008 (online)

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Abstract

A strategy for the total synthesis of vinigrol is detailed with two key steps - oxidative dearomatization and intramolecular Diels-Alder cycloaddition - providing the cis-decalin core. A novel and mild means for the formation of ortho-quinone methides is also described.

Key words

vinigrol - oxidative dearomatization - cycloaddition - ortho-quinone methide - trichloroacetylisocyanate

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18

See Supporting Information.

23

Determined by NOESY correlation.

24

Amusingly, a characterization sample of the intermediate quinol, saved in a -20 ˚C freezer, was found, after one year, to have completely converted into the cycloadduct 27.