Publication: Studies toward the total synthesis of naturally occurring pyranonaphthoquinones from ventilago harmandiana
Issued Date
2012-05-28
Resource Type
ISSN
13653075
00334545
00334545
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2-s2.0-84861362002
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Mahidol University
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SCOPUS
Bibliographic Citation
Pure and Applied Chemistry. Vol.84, No.6 (2012), 1435-1443
Suggested Citation
Sopanat Kongsriprapan, Chutima Kuhakarn, Pramchai Deelertpaiboon, Kanda Panthong, Patoomratana Tuchinda, Manat Pohmakotr, Vichai Reutrakul Studies toward the total synthesis of naturally occurring pyranonaphthoquinones from ventilago harmandiana. Pure and Applied Chemistry. Vol.84, No.6 (2012), 1435-1443. doi:10.1351/PAC-CON-11-08-24 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/13916
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Title
Studies toward the total synthesis of naturally occurring pyranonaphthoquinones from ventilago harmandiana
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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.