• Archives of Pharmacal Research
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• 제29권8호
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• pp.624-626
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• 2006

Four known butenolides were isolated from the ethyl acetate extracts of the culture broth of the marine-derived bacterium, Streptoverticillium luteoverticillatum, by bioassay-guided fractionation. The structures were identified on the basis of spectral data. The absolute configuration of compound (1) was determined by CD spectrum for the first time. Compounds 1-4 showed in vitro cytotoxicity against the murine lymphoma P388 and human leukemia K562 cell lines. This is the first report on the isolation of butenolides from the marine bacterium, Streptoverticillium luteoverticillatum, and their cytotoxic activities.

• Bulletin of the Korean Chemical Society
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• 제32권spc8호
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• pp.2911-2915
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• 2011

Efficient synthetic method for the preparation of ethyl 2-aryl-2,3-alkadienoates through Pd-catalyzed selective allenyl cross-coupling reactions of aryl iodides with organoindiums generated in situ from indium and ethyl 4-bromo-2-alkynoate was developed. The cyclization reaction of ethyl 2-aryl-2,3-alkadienoates catalyzed by $AuCl_3$ and AgOTf in the presence of AcOH or TfOH produced various ${\alpha}$-aryl ${\gamma}$-butenolides or ${\gamma}$-substituted ${\alpha}$-aryl ${\gamma}$-butenolides.

• 대한화학회지
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• 제47권3호
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• pp.229-236
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• 2003

Cyclobutenedions을 lithium trimethylsilylacetylene과 반응시키고 물로 반응을 정지시키면 butenolides가 생성된다. 이 색다른 반응을 위해 allene을 intermediate로 하는 기전을 제안하였다. 이는 trimethylsilyl group이 너무 크기 때문에 보통의 diradical intermediate는 형성이 어렵고, allene이 ${\alpha}$-silyl group에 의해 안정화되기 때문이라고 사료된다.

• Bulletin of the Korean Chemical Society
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• 제33권5호
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• pp.1781-1784
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• 2012

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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• pp.190.3-190.3
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• 2003

Three new butenolides (1-3), and a new cyclopentenone derivative (4) were isolated from a marine sponge Homaxinella sp. by bioactivity guided fractionation. The gross structures were established on the basis of NMR and MS analyses. The stereochemistry of the butenolides and cyclopentenone derivative was defined on the basis of optical rotation and CD spectroscopy. The compounds were tested against a panel of five human solid tumor cell lines and displayed marginal to significant cytotoxicity.

• 대한화학회지
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• 제63권5호
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• pp.346-351
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• 2019

Mannich-type reactions of cyclic N-sulfimines with 2-trimethylsiloxyfuran and pyrazolin-5-one have been developed using phosphoric acid (PA) as an organocatalyst. 2-Trimethylsiloxyfuran underwent a vinylogous Mannich-type reaction with cyclic N-sulfimines in the presence of the PA catalyst to give sulfamidate ${\gamma}$-butenolides in good yields and with high diastereoselectivities (up to 90% yield and 7:1 dr). In addition, the reaction between pyrazolin-5-one and a diverse range of cyclic N-sulfimines provided access to sulfamidates in good to high yields (up to 94% yield).

• Bulletin of the Korean Chemical Society
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• 제30권5호
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• pp.1012-1020
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• 2009

We developed an efficient three-step synthetic protocol of $\gamma$-hydroxybutenolides starting from the Baylis-Hillman adducts: (i) bromination, (ii) Barbier reaction and (iii) one-pot $K_2CO_3$-mediated synthesis of $\gamma$-hydroxybutenolides. In addition, we showed the synthetic applicability of butenolides including self-dimerization, conjugate addition reaction, and alkylations.