State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, P. R China.
Org Lett. 2014 May 16;16(10):2700-3. doi: 10.1021/ol500978k. Epub 2014 Apr 29.
Cernupalhine A (1) is a trace Lycopodium alkaloid (0.7 mg) possessing a new C17N skeleton with an unusual hydroxydihydrofuranone motif newly isolated from Palhinhaea cernua L. Its complete structural assignment, including absolute stereochemistry, was established through a combination of high-field NMR techniques and computational methods and further unequivocal confirmation by the first asymmetric total synthesis. Following the first total synthesis of lobscurinine (3), 1 was achieved via regio- and stereoselective cyanide ion addition and subsequent acid treatment.
Cernupalhine A (1) 是一种痕量石松生物碱（0.7mg），具有一个新的 C17N 骨架，其中含有一个不寻常的羟二氢呋喃酮基序，是从 Palhinhaea cernua L. 中分离得到的。其完整的结构确定，包括绝对立体化学，是通过高场 NMR 技术和计算方法的组合以及首次不对称全合成得到的进一步明确证实。在首次全合成 lobscurinine (3) 之后，通过区域和立体选择性氰离子加成和随后的酸处理来实现 1。
