Total synthesis of (-)-irciniastatin B and structural confirmation via chemical conversion to (+)-irciniastatin A (psymberin).
The total synthesis and structural confirmation of the marine sponge cytotoxin (-)-irciniastatin B has been achieved via a unified strategy employing a late-stage, selective deprotection/oxidation sequence that provides access to both (+)-irciniastatin A (psymberin) and (-)-irciniastatin B.
Department of Chemistry, Laboratory for Research on the Structure of Matter and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
Chihui
C
An
Adam T
AT
Hoye
Amos B
AB
Smith
D000818:Animals; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D003603:Cytotoxins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008386:Marine Biology; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
D003374:Coumarins; D003603:Cytotoxins; C483487:irciniastatin B; C498383:psymberin