444753-72-4Relevant academic research and scientific papers
Total Synthesis of Dapholdhamine B and Dapholdhamine B Lactone
Guo, Lian-Dong,Hou, Jieping,Tu, Wentong,Zhang, Yan,Zhang, Yue,Chen, Louxi,Xu, Jing
, p. 11713 - 11720 (2019)
The intriguing structural complexity and bioactivities of the Daphniphyllum alkaloids have long attracted much attention. Herein, we report the first and enantioselective total synthesis of Daphniphyllum alkaloid dapholdhamine B and its lactone derivative. The chemical structure of dapholdhamine B contains a unique aza-adamantane core skeleton and eight contiguous stereocenters, including three contiguous fully substituted stereocenters, which present a formidable synthetic challenge. This concise approach used to achieve the first synthesis of an aza-adamantane natural product features a vinylogous Mannich reaction, an optimized α-bromo-α,β-unsaturated ketone synthesis, a substrate-dependent intramolecular aza-Michael addition, a key annulation via amide activation, an SN2′-type lactonization, and a facile Horner-Wadsworth-Emmons reaction that converts the hemiacetal moiety to the corresponding homologated carboxylic acid.
A Fischer indolization strategy toward the total synthesis of (–)-goniomitine
Pritchett, Beau P.,Kikuchi, Jun,Numajiri, Yoshitaka,Stoltz, Brian M.
, p. 1245 - 1253 (2019/12/11)
A Fischer indolization strategy toward the core of (–)-goniomitine is reported. Initial investigations into the Pd-catalyzed asymmetric allylic alkylation of dihydropyrido[1,2-a]indolone (DHPI) substrates are also discussed.
Synthesis of 7-substituted benzolactam-V8s and their selectivity for protein kinase C isozymes.
Ma, Dawei,Tang, Guozhi,Kozikowski, Alan P
, p. 2377 - 2380 (2007/10/03)
[reaction: see text] Condensation of L-valine benzyl ester toluenesulfonic acid salt with a substituted cyclohexadione followed by aromatization with the assistance of NBS provides an N-aryl L-valine benzyl ester. This intermediate is converted into 7-sub
