Tandem Diels-Alder/fragmentation approach to the synthesis of eleutherobin.
[reaction: see text] A synthesis of 28, the carbon framework of the eleutherobin aglycone, is reported in a 15-step sequence from readily available starting materials. The tandem Diels-Alder reaction of 6 and 7 to produce 18, in which three new rings and six new stereocenters are formed, is a key step in the reaction sequence.
Winkler
Jeffrey D
JD
Department of Chemistry, The University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. winkler@sas.upenn.edu
Quinn
Kevin J
KJ
MacKinnon
Colin H
CH
Hiscock
Steven D
SD
McLaughlin
Emily C
EC
D000470:Alkaloids / Q000138:chemical synthesis*; D037421:Anthozoa / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D003500:Cyclization; D004224:Diterpenes; D007202:Indicators and Reagents; D008968:Molecular Conformation
D000470:Alkaloids; D000970:Antineoplastic Agents; D004224:Diterpenes; D007202:Indicators and Reagents; C109551:eleutherobin