Advances in Lewis acid controlled carbon-carbon bond-forming reactions enable a concise and convergent total synthesis of bullatacin.
Lewis acids control regioselectivity in the alkylation of epi-chlorohydrin and the stereochemistry of an alkyne addition to set the C24/C23 anti relationship. These advances facilitate an efficient total synthesis of bullatacin in 13.3% overall yield from commercial starting materials.
Zhao
Hongda
H
Department of Chemistry, University of Western Ontario, London, ON N6A 5B7, Canada.
Gorman
Jeffrey S T
JS
Pagenkopf
Brian L
BL
D000143:Acids / Q000737:chemistry*; D000478:Alkylation; D005663:Furans / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000143:Acids; D005663:Furans; C061022:bullatacin