1365993-54-9Relevant academic research and scientific papers
(-)-Pseudodistomin E: First Asymmetric Synthesis and Absolute Configuration Assignment
Davies, Stephen G.,Fletcher, Ai M.,Roberts, Paul M.,Thomson, James E.,Zimmer, David
, p. 1638 - 1641 (2017)
(-)-Pseudodistomin E has been prepared for the first time, allowing its structure and absolute configuration to be confirmed. The established conjugate addition of lithium (S)-N-allyl-N-(α-methyl-p-methoxybenzyl)amide to methyl (E,E)-hepta-2,5-dienoate generated the C(2)-stereocenter, and iodolactonisation of a derivative generated the remaining two stereogenic centers. Ensuing iodide displacement was achieved using a tethering strategy, to introduce the nitrogen atom to C(5). Decarboxylative coupling of a carboxylic acid with a dialkylzinc reagent completed construction of the tridecadienyl chain.
Polysubstituted piperidines via iodolactonization: Application to the asymmetric synthesis of (+)-pseudodistomin D
Davies, Stephen G.,Fletcher, Ai M.,Lee, James A.,Roberts, Paul M.,Russell, Angela J.,Taylor, Rachael J.,Thomson, Anthony D.,Thomson, James E.
supporting information; experimental part, p. 1672 - 1675 (2012/06/30)
Conjugate addition of lithium (S)-N-allyl-N-(α-methyl-p- methoxybenzyl)amide to methyl (E,E)-hepta-2,5-dienoate furnished the corresponding β-amino ester. N-Protecting group manipulation, ring-closing metathesis, and ester hydrolysis gave enantiopure [N(1
