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  • Title: A tether controlled exo-selective trans-annular Diels-Alder (TADA) reaction.
    Author: Felzmann W, Arion VB, Mieusset JL, Mulzer J.
    Journal: Org Lett; 2006 Aug 17; 8(17):3849-51. PubMed ID: 16898833.
    Abstract:
    [reaction: see text] A fully substrate controlled stereoselective route to construct cis-hexahydronaphthalene 4 is described starting from nonracemic butenolide 6. The key step is an exo-selective transannular Diels-Alder reaction (TADA) of tetraene 5, whose intrinsic constraint allows selective formation of one stereodefined product. Compound 4 is a key intermediate in the synthesis of the novel antibiotic branimycin (1).
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