Synthesis of the C7-C15 trans decalin portion of the natural antibiotic tetrodecamycin.
[reaction: see text] The tandem oxy-Cope/ene/Claisen rearrangement has been developed in our laboratory as a powerful method for rapid construction of complex Decalin cores. Herein, we describe the use of this method to generate the Decalin core of the natural antibiotic tetrodecamycin (1) bearing six contiguous stereocenters.
Warrington
Jeffrey M
JM
Department of Chemistry, 10 Marie Curie, University of Ottawa, Ottawa, Ontario, Canada K1N 6N5.
Barriault
Louis
L
D000900:Anti-Bacterial Agents / Q000737:chemistry*; D005663:Furans / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D005663:Furans; D009281:Naphthalenes; C087129:tetrodecamycin; C007229:decalin