A rapid entry into the dynemicin core structure: remarkable solvent effect on an η2-hexacarbonyldicobalt propargylic cation cyclization
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 7,p. 544-546
- https://doi.org/10.1039/c39910000544
Abstract
3-(tert-Butyldimethylsilyloxy)quinoline 8 on treatment with the diynene 9 gave the diynene 10(64%), and deprotection of 10 gave 11(88%) which was converted into the η2-Co2(CO)6 adduct 12; treatment of 12 with (CF3SO2)2O in CH2Cl2–MeNO2 at –10°C gave the cyclized product 13(43%), and decomplexation of 13 using I2–THF produced the stable azabicyclo[7.3.1]tridecadiynene core structure 7 of the antitumour antibiotic dynemicin 1.Keywords
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