Chromium-mediated asymmetric synthesis of both enantiomers of acetoxytubipofuran.
Both enantiomers of acetoxytubipofuran were synthesized using enantioselective and diastereoselective dearomatization sequences starting from the benzaldehyde chromium tricarbonyl complex. Following aldol condensation, a sequence involving Pd-catalyzed allylic substitution was used in the synthesis of the (-)-enantiomer, whereas the (+)-enantiomer was reached via an Eschenmoser-Claisen rearrangement. Chiroptical data show that a revision of the previously assigned absolute configuration of the natural product is required.
Kündig
E Peter
EP
Department of Organic Chemistry, University of Geneva, 30 Quai Ernest Ansermet, 1211 Geneva 4, Switzerland. peter.kundig@chiorg.unige.ch
Cannas
Rita
R
Laxmisha
Mundruppady
M
Ronggang
Liu
L
Tchertchian
Sylvie
S
D000818:Animals; D002857:Chromium / Q000737:chemistry*; D003063:Cnidaria / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis*
D005663:Furans; D013729:Terpenes; C475124:acetoxytubipofuran; D002857:Chromium