Total Synthesis of the Furaquinocins Takeshi Saito Takao Suzuki Munetsugu Morimoto Chikako Akiyama Takashi Ochiai Kazuhiro Takeuchi Takashi Matsumoto Keisuke Suzuki 10.1021/ja982403t.s001 https://acs.figshare.com/articles/journal_contribution/Total_Synthesis_of_the_Furaquinocins/3671901 A viable synthetic route to the furaquinocin-class antibiotics is described. The key steps include (1) Co-complex mediated stereospecific 1,2-shift of an alkynyl group (<b>9</b> → <b>6</b>) to establish the C(2)−C(3) stereochemical relationship, (2) efficient construction of furanonaphthalene <b>20</b> from the sodium carboxylate derived from ester <b>19</b>, and (3) stereoselective methylene transfer reaction to aldehyde <b>21</b> to establish the three contiguous stereogenic centers, C(2), C(3), and C(10). The stereodefined epoxide <b>23</b>, thus obtained, served as a versatile intermediate in divergent syntheses of four congeners of this class of natural products, furaquinocins A (<b>1a</b>), B (<b>1b</b>), D (<b>1d</b>), and H (<b>1h</b>), by changing the vinylic nucleophiles. 1998-10-30 00:00:00 antibiotic stereoselective sodium carboxylate ester 19 alkynyl group vinylic nucleophiles synthese furanonaphthalene 20 methylene stereochemical relationship stereodefined epoxide 23 aldehyde 21 construction congener stereogenic centers shift Total Synthesis stereospecific furaquinocin transfer Furaquinocin