27270-89-9Relevant articles and documents
Parasitenone, a new epoxycyclohexenone related to gabosine from the marine-derived fungus Aspergillus parasiticus
Son, Byeng Wha,Choi, Jin Seok,Kim, Jung Chul,Nam, Ki Wan,Kim, Dong-Soo,Chung, Hae Young,Kang, Jung Sook,Choi, Hong Dae
, p. 794 - 795 (2002)
Bioassay-guided fractionation of an organic extract of the broth from the marine-derived fungus culture of Aspergillus parasiticus led to the isolation and subsequent structural elucidation of a new gabosine derivative, parasitenone (1), and two known benzyl alcohols, 3-chloro-4,5-dihydroxybenzyl alcohol (2) and gentisyl alcohol (3). The benzyl alcohols (2, 3) were identified as the principal free radical scavenging components. Parasitenone (1) also showed moderate activity in the free radical scavenging assay.
Stereo- and enantio-controlled synthesis of two naturally occurring polyoxygenated cyclohexenemethanols, (+)-epiepoxydon and (-)-phyllostine, via catalytic asymmetrization of a meso substrate
Kamikubo, Takashi,Hiroya, Kou,Ogasawara, Kunio
, p. 499 - 502 (1996)
Two naturally occurring polyoxygenated cyclohexenemethanols, (+)-epiepoxydon and (-)-phyllostine, have been first synthesized in stereo- and enantio-controlled manner using a chiral cyclohexadienol synthon prepared by catalytic asymmetrization of a meso substrate. The synthesis has verified the proposed absolute structures of these natural products which have been deduced by CD measurements.
Synthesis of (+)-Epoxydon, (–)-Phyllostine, (–)-RKTS 33, and (–)-Parasitenone Featuring Selective Sulfonylation and Oxirane Ring Closure of Aldol Cyclization Products
Chen, Xiaochuan,Jia, Junhao,Jiang, Yimin,Shui, Feng,Yang, Xing,Zhou, Qin
, (2020/07/04)
Two new synthetic approaches to anhydrogabosines are developed from the polyoxygenated aldol cyclization intermediates, bearing different O-protecting groups, which were transformed to various gabosine-type cyclitols. Selective sulfonylation on the required hydroxyl group of the intermediates and the subsequent oxirane ring closure are employed as the key steps in both approaches, by which (+)-epoxydon, (–)-phyllostine, (–)-RKTS 33, and (–)-parasitenone were synthesized from δ-d-gluconolactone.
Efficient synthesis of (±)-parasitenone, a novel inhibitor of NF-κB
Saitoh, Tsuyoshi,Suzuki, Eriko,Takasugi, Arisa,Obata, Rika,Ishikawa, Yuichi,Umezawa, Kazuo,Nishiyama, Shigeru
scheme or table, p. 5383 - 5386 (2010/08/06)
Dehydroxymethylepoxyquinomicin (DHMEQ, 1) is a novel nuclear factor-κB (NF-κB) inhibitor that inhibits DNA binding of NF-κB components including p65. To inspect its biological activity of 1, we synthesized parasitenone (3), possessing the common epoxycyclohexenone moiety of 1. Assessment of the inhibitory activity against NF-κB indicated that the epoxycyclohexenone moiety is the most essential element for the NF-κB inhibitory activity and the salicylic acid moiety may contribute the binding efficiency and specificity.
Enantioselective total synthesis of epoxyquinone natural products (-)-phyllostine, (+)-epoxydon, (+)-epiepoxydon and (-)-panepophenanthrin: Access to versatile chiral building blocks through enzymatic kinetic resolution
Mehta, Goverdhan,Islam, Kabirul
, p. 7683 - 7687 (2007/10/03)
A new enzyme mediated protocol to access versatile chiral building blocks for the synthesis of epoxyquinone natural products is delineated. Total syntheses of (-)-phyllostine, (+)-epoxydon, (+)-epiepoxydon and (-)-panepophenanthrin have been accomplished to demonstrate the efficacy of this approach.
Total synthesis of (+)-epiepoformin and (-)-phyllostine
Okamura, Hiroaki,Shimizu, Hideki,Yamashita, Naomi,Iwagawa, Tetsuo,Nakatani, Munehiro
, p. 10159 - 10164 (2007/10/03)
An efficient asymmetric total synthesis of naturally occurring cyclohexeneoxides, (+)-epiepoformin and (-)-phyllostine has been achieved using the chiral building block available from the base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone. Since (-)-theobroxide was derived from the same precursor of (+)-epiepoformin, the formal total synthesis of (-)-theobroxide has also been achieved.
Preparation of a synthetic equivalent of chiral methyl 2,5- dihydroxycyclohexane-1,4-dienecarboxylate
Yoshida, Naoyuki,Konno, Hiroyuki,Kamikubo, Takashi,Takahashi, Michiyasu,Ogasawara, Kunio
, p. 3849 - 3857 (2007/10/03)
A chiral tricyclic diol, serving as a synthetic equivalent of chiral methyl 2,5-dihydroxycyclohexane-1,4-dienecarboxylate, has been prepared in both enantiomeric forms by employing a lipase-mediated kinetic resolution in vinyl acetate.
