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