Kalshetti Manojkumar G, Argade Narshinha P
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411008, India.
Academy of Scientific and Innovative Research (AcSIR), New Delhi 110025, India.
ACS Omega. 2018 May 17;3(5):5308-5316. doi: 10.1021/acsomega.8b00587. eCollection 2018 May 31.
Starting from indolylmaleimide, concise and efficient total synthesis of (±)--subincanadine C was described via stereoselective Wittig olefination, base-induced selective mono-prenylation, regioselective Grignard reaction, diastereoselective Pictet-Spengler cyclization, regioselective oxidative carbon-carbon double-bond cleavage, one-pot reductions, and intramolecular cyclization pathway. An attempted synthesis of (±)-subincanadine C via diastereoselective Grignard addition to the α,β-unsaturated γ-lactam or diastereoselective reduction of a carbon-carbon double bond also resulted in yet another route to (±)--subincanadine C.
从吲哚马来酰亚胺出发，通过立体选择性维蒂希烯烃化反应、碱诱导的选择性单异戊烯基化反应、区域选择性格氏反应、非对映选择性皮克特-施彭格勒环化反应、区域选择性氧化碳-碳双键裂解反应、一锅法还原反应以及分子内环化途径，描述了（±）-次因卡纳定C的简洁高效全合成。尝试通过非对映选择性格氏加成到α,β-不饱和γ-内酰胺或非对映选择性还原碳-碳双键来合成（±）-次因卡纳定C，这也产生了另一条合成（±）-次因卡纳定C的路线。
