Regioselective synthesis of the tricyclic core of lateriflorone.
An efficient synthetic approach to the tricyclic core 8 of lateriflorone is described. Essential to the synthesis was the implementation of a biomimetic tandem Claisen/Diels-Alder reaction that produced the desired tricyclic scaffold as a single isomer. A rationalization of the excellent regio and stereoselectivity of this transformation is also proposed. [reaction: see text]
Tisdale
Eric J
EJ
Department of Chemistry and Biochemistry, University of California San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0358, USA.
Li
Hongmei
H
Vong
Binh G
BG
Kim
Sun Hee
SH
Theodorakis
Emmanuel A
EA
D003500:Cyclization; D029760:Garcinia / Q000737:chemistry; D008968:Molecular Conformation; D011083:Polycyclic Compounds / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013148:Spironolactone / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014966:Xanthenes / Q000737:chemistry; D044004:Xanthones
D011083:Polycyclic Compounds; D013141:Spiro Compounds; D014966:Xanthenes; D044004:Xanthones; C476169:lateriflorone; D013148:Spironolactone; C009689:xanthone