332843-99-9Relevant academic research and scientific papers
Synthesis of macrocyclic precursors of lankacidins using Stille reactions of 4-(2-iodo-alkenyl)azetidinones and related compounds for ring closure
Brain, Christopher T.,Chen, Anqi,Nelson, Adam,Tanikkul, Nongluk,Thomas, Eric J.
supporting information; experimental part, p. 6613 - 6625 (2010/10/19)
In the context of a proposed total synthesis of lankacidins, the synthesis of 4-(2-iodo-alkenyl)azetidinones and their participation in Stille coupling reactions have been investigated. 1-tert-Butyldimethylsilyl-4-(2-iodoethenyl) azetidinone was found to
An approach to the total synthesis of lankacidins: Synthesis of the requisite building blocks
Brain, Christopher T.,Chen, Anqi,Nelson, Adam,Tanikkul, Nongluk,Thomas, Eric J.
, p. 1247 - 1250 (2007/10/03)
A strategy for a total synthesis of lankacidin C 1 is outlined and the requisite building blocks synthesised. The azetidinone 4 was prepared from methyl but-2-ynoate 6 via a route which features the stereoselective addition of a tributyltin cuprate to the alkyne, an asymmetric aldol condensation and formation of the azetidinone by an intramolecular Mitsunobu reaction. The aldehyde 3 was prepared from dimethyl malate 18 and the sulfone 3 from prop-2-ynol 27 again using asymmetric aldol reactions as key steps.
