Stereoselective approach to the racemic oxatetracyclic core of platensimycin.
A highly stereoselective synthesis of the racemic oxatetracyclic core of platensimycin has been accomplished from a known bicyclic epoxy lactone by an 11-step sequence that involves a Diels-Alder cyclcoaddition to construct its cis-decalenone structural motif with complete regio- and stereoselectivity and a ring-closing metathesis to establish its whole carbon framework.
Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981-8555, Japan.
Sakuya
S
Horii
Munefumi
M
Torihata
Tomohiro
T
Nagasawa
Shigefumi
S
Kuwahara
D000218:Adamantane / Q000138:chemical synthesis* / Q000737:chemistry*; D062365:Aminobenzoates / Q000138:chemical synthesis* / Q000737:chemistry*; D000813:Anilides / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D062365:Aminobenzoates; D000813:Anilides; D011083:Polycyclic Compounds; D000218:Adamantane; C510909:platensimycin