Biomimetic total synthesis of forbesione and desoxymorellin utilizing a tandem Claisen/Diels--Alder/Claisen rearrangement.
A concise synthesis of forbesione (1) and desoxymorellin (3) is presented. Central to the strategy is a biomimetic Claisen/Diels-Alder/Claisen reaction cascade that proceeds in a regioselective manner and produces the desired scaffold exclusively. The observed regioselectivity and product distribution of the Claisen/Diels-Alder/Claisen reaction are attributed to the electronic effects of the xanthone oxygen (O10), the C9 carbonyl group and the nature of the C1 functionality.
Tisdale
Eric J
EJ
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla 92093-0358, USA.
Slobodov
Irina
I
Theodorakis
Emmanuel A
EA
D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D029760:Garcinia / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008956:Models, Chemical; D008968:Molecular Conformation; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D006571:Heterocyclic Compounds; C482270:desoxymorellin; C482271:forbesione