Enantioselective formal total synthesis of dihydrospirotryprostatin B

IF 1.3 3区 医学 Q3 CHEMISTRY, APPLIED Journal of Asian Natural Products Research Pub Date : 2024-06-01 DOI:10.1080/10286020.2024.2355504
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Abstract

Spirotryprostatins are representative members of medicinally interesting bioactive molecules of the spirooxindole natural products. In this communication, we present a novel enantioselective total synthesis of the spirooxindole alkaloid dihydrospirotryprostatin B. The synthesis takes advantage of copper-catalyzed tandem reaction of o-iodoanilide chiral sulfinamide derivatives with alkynone to rapidly construct the key quaternary carbon stereocenter of the natural product dihydrospirotryprostatin B.

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二氢螺前列素 B 的对映体选择性正式全合成。
螺旋前列腺素是螺旋吲哚类天然产物中具有药用价值的生物活性分子的代表成员。该合成利用铜催化的邻碘苯胺手性亚磺酰胺衍生物与炔酮的串联反应,快速构建了天然产物二氢螺螺昔他丁 B 的关键季碳立体中心。
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来源期刊
CiteScore
3.20
自引率
5.90%
发文量
47
审稿时长
2.3 months
期刊介绍: The Journal of Asian Natural Products Research (JANPR) publishes chemical and pharmaceutical studies in the English language in the field of natural product research on Asian ethnic medicine. The journal publishes work from scientists in Asian countries, e.g. China, Japan, Korea and India, including contributions from other countries concerning natural products of Asia. The journal is chemistry-orientated. Major fields covered are: isolation and structural elucidation of natural constituents (including those for non-medical uses), synthesis and transformation (including biosynthesis and biotransformation) of natural products, pharmacognosy, and allied topics. Biological evaluation of crude extracts are acceptable only as supporting data for pure isolates with well-characterized structures. All published research articles in this journal have undergone rigorous peer review, based on initial editor screening and anonymized refereeing by at least two expert referees.
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