A tether controlled exo-selective trans-annular Diels-Alder (TADA) reaction.
[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).
Felzmann
Wolfgang
W
Institut für Organische Chemie, Universität Wien, Währingerstrasse 38, A-1090 Vienna, Austria.
Arion
Vladimir B
VB
Mieusset
Jean-Luc
JL
Mulzer
Johann
J
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D018942:Macrolides; C516575:branimycin