Efficient synthesis of polycycles bearing prenylated, geranylated, and farnesylated citrans: application to 3 '-prenylrubranine and petiolin D regioisomer

Title
Efficient synthesis of polycycles bearing prenylated, geranylated, and farnesylated citrans: application to 3 '-prenylrubranine and petiolin D regioisomer
Author(s)
이용록왕설
Keywords
PYRANOCHALCONE NATURAL-PRODUCTS; CONCISE TOTAL-SYNTHESIS; DIELS-ALDER REACTION; ALPHA,BETA-UNSATURATED ALDEHYDES; ESSENTIAL OILS; ORIXALONE-D; CONSTITUENTS; HASHISH; (+)-HEXAHYDROCANNABINOL; (-)-HEXAHYDROCANNABINOL
Issue Date
201111
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Citation
TETRAHEDRON, v.67, no.47, pp.9179 - 9184
Abstract
Efficient synthetic routes for biologically interesting polycycles with prenylated, geranylated, and farnesylated citrans were developed from several trihydroxybenzenes with prenyl, geranyl, and farnesyl groups on the benzene rings. Ethylenediamine diacetate-catalyzed cyclization by a domino aldol-type/electrocyclization/H-shift/hetero Diels-Alder reaction of prenylated, geranylated, and farnesylated trihydroxybenzenes with citral or trans,trans-farnesal provided a variety of tetracycles bearing prenylated, geranylated, and farnesylated citrans. The mechanistic pathway for regio- and stereochemistry of synthesized polycycles was described. As an application of this methodology, 3'-prenylrubranine and petiolin D regioisomer were first synthesized. (C) 2011 Elsevier Ltd. All rights reserved.
URI
http://hdl.handle.net/YU.REPOSITORY/24305http://dx.doi.org/10.1016/j.tet.2011.09.075
ISSN
0040-4020
Appears in Collections:
공과대학 > 화학공학부 > Articles
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