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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 1
BKCSDE 32(1)
January 20, 2011 

Concise Synthesis of (±)-Rhinacanthin A, Dehydro α-lapachone, and β-Lapachone, and Pyranonaphthoquinone Derivatives   
Xue Wang, Ye Chen, Yong Rok Lee*
Pyranonaphthoquinones, Rhinacanthin A, Dehydro-α-lapachone, β-Lapachone
A concise synthesis of (±)-rhinacanthin A is achieved in two steps by epoxidation of dehydro-α-lapachone, followed by chemo- and regioselective reduction. Dehydro-α-lapachone was also synthesized in two steps starting from 4-methoxy- 1-naphthol by ethylenediamine diaetate (EDDA)-catalyzed benzopyran formation and a CAN-mediated oxidation reaction. β-Lapachone was synthesized in three steps from 4-methoxy-1-naphthol by benzopyran formation, catalytic hydrogenation, and Jones oxidation. As additional reactions, synthesis of pyranonaphthoquinone derivatives with the pyranokunthone B skeleton has been achieved in a single step from readily available 2-hydroxy-6-methoxy- 1,4-naphthoquinone and 2-hydroxy-7-methoxy-1,4-naphthoquinone.
153 - 156
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