A tether controlled exo-selective trans-annular Diels-Alder (TADA) reaction |
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| Authors: | Felzmann Wolfgang Arion Vladimir B Mieusset Jean-Luc Mulzer Johann |
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| Affiliation: | Institut für Organische Chemie, Universit?t Wien, W?hringerstrasse 38, A-1090 Vienna, Austria. |
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| 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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