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Title: Studies toward the total synthesis of naturally occurring pyranonaphthoquinones from ventilago harmandiana
Authors: Sopanat Kongsriprapan
Chutima Kuhakarn
Pramchai Deelertpaiboon
Kanda Panthong
Patoomratana Tuchinda
Manat Pohmakotr
Vichai Reutrakul
Mahidol University
Prince of Songkla University
Keywords: Chemical Engineering;Chemistry
Issue Date: 28-May-2012
Citation: Pure and Applied Chemistry. Vol.84, No.6 (2012), 1435-1443
Abstract: The enantioselective synthesis of a naturally occurring pyranonaphthoquinone isolated from a Thai endemic plant, Ventilago harmandiana, has been achieved. L-Rhamnose and gallic acid were used as the starting materials. A new C-1-glycosidation of L-rhamnal with trimethyl aluminum in the presence of a catalytic amount of ytterbium(III) triflate was developed. A new reagent, PhSCF 2 H/SnCl 4 , for the formylation of partially deactivated and hindered aromatic compounds has been introduced. Phenylthiophthalide was used efficiently as a cycloannulating agent in the Hauser cycloannulation reaction, employing slightly excess lithium t-butoxide as a base with a catalytic amount of lithium chloride. The synthetic route developed is applicable for the synthesis of other analogues with substituents at the aromatic and pyran rings. © 2012, IUPAC.
ISSN: 13653075
Appears in Collections:Scopus 2011-2015

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