Concise Synthesis of (+/-)-Rhinacanthin A, Dehydro alpha-Lapachone, and beta-Lapachone, and Pyranonaphthoquinone Derivatives

Title
Concise Synthesis of (+/-)-Rhinacanthin A, Dehydro alpha-Lapachone, and beta-Lapachone, and Pyranonaphthoquinone Derivatives
Author(s)
이용록왕설[왕설]진엽[진엽]
Keywords
PROSTATE-CANCER CELLS; TABEBUIA-AVELLANEDAE; NAPHTHOQUINONES; APOPTOSIS; CONSTITUENTS; INHIBITORS; INDUCTION; RHINACANTHIN; SUPEROXIDE; TARGET
Issue Date
201101
Publisher
KOREAN CHEMICAL SOC
Citation
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v.32, no.1, pp.153 - 156
Abstract
A concise synthesis of (+/-)-rhinacanthin A is achieved in two steps by epoxidation of dehydro-alpha-lapachone, followed by chemo- and regioselective reduction. Dehydro-alpha-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. beta-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-methoxy1,4-naphthoquinone and 2-hydroxy-7-methoxy-1,4-naphthoquinone.
URI
http://hdl.handle.net/YU.REPOSITORY/25777http://dx.doi.org/10.5012/bkcs.2011.32.1.153
ISSN
0253-2964
Appears in Collections:
공과대학 > 화학공학부 > Articles
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