1083169-29-2Relevant academic research and scientific papers
The enantioselective total synthesis and unambiguous proof of the absolute stereochemistry of pervilleine C
Kulkarni, Ketav,Zhao, Anne Y.,Purcell, Anthony W.,Perlmutter, Patrick
, p. 2209 - 2212 (2008)
The first enantioselective, total synthesis of the naturally occurring, potent cancer MDR reversal agent pervilleine C is reported. Each enantiomer of the natural product has been prepared as well as the enantiomers of the corresponding 8-oxa-pervilleine
A novel and versatile method for the enantioselective syntheses of tropane alkaloids
Mao, Zhongyi,Huang, Suyu,Gao, Longhui,Wang, Aie,Huang, Peiqiang
, p. 252 - 264 (2014/03/21)
A full account of the novel and flexible approach to hydroxylated 8-azabicyclo[3,2,1]octan-3-ones and 9-azabicyclo[3,3,1] nonan-3-ones is presented. Using keto-lactams as the starting materials, this two-step method consists of silyl enol ether formation with TBDMSOTf, lactam activation with Tf2O/DTBMP, and halide-promoted cyclization. Radical dechlorination of the resulting 1-halotropan-3-ones led to the corresponding hydroxylated tropan-3-ones, which can be hydrogenated to yield 3α,6β- dihydroxytropanes. Starting from optically active keto-lactams, the method has been applied to the enantioselective syntheses of (+)-(1S,3S,5R,6S)-pervilleine C (6), (+)-(1S,3R,5S,6R)-valeroidine (3), (+)-(1S,3S,5R,6S)-dibenzoyloxytropane (8), and (+)-(1S,3S,5R,6S)-merredissine (9).
Versatile construction of functionalized tropane ring systems based on lactam activation: Enantioselective synthesis of (+)-pervilleine B
Huang, Su-Yu,Chang, Zong,Tuo, Shi-Chuan,Gao, Long-Hui,Wang, Ai-E,Huang, Pei-Qiang
supporting information, p. 7088 - 7090 (2013/09/02)
The halo-assisted intramolecular addition of silyl enol ethers with in situ activated lactams yielded (hydroxylated) 1-halo-8-azabicyclo[3,2,1]octane and 1-halo-9-azabicyclo[3,3,1]nonane ring systems, which provided an easy enantioselective access to 6β-s
