化学
全合成
分子内力
硼氢化
立体化学
戒指(化学)
酒
生物碱
组合化学
有机化学
催化作用
作者
Lin Liu,Trevor L. Olson,John L. Wood
出处
期刊:Organic Letters
[American Chemical Society]
日期:2024-08-23
卷期号:26 (35): 7341-7346
标识
DOI:10.1021/acs.orglett.4c02516
摘要
Herein we describe a total synthesis of the heterodimeric securinega alkaloid (−)-flueggeacosine C (8). The convergent synthetic strategy is based on a Liebeskind–Srogl cross-coupling reaction that combines a benzoquinolizidine fragment with a securinine-type alkaloid. An acyloxy nitroso ring-expansion was employed as the key step in accessing benzoquinolizidine 9, and a novel intramolecular Diels–Alder reaction of an allenic acid-containing pyridone expeditiously delivers the skeleton of the securinine-type fragment (16). Finally, a Cu-catalyzed hydroboration-oxidation sequence was employed to regio- and diastereoselectively introduce the secondary alcohol found in 8.
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