Brain, Christopher T.; Chen, Anqi; Nelson, Adam; Tanikkul, Nongluk; Thomas, Eric J. published the artcile< Synthesis of macrocyclic precursors of lankacidins using Stille reactions of 4-(2-iodo-alkenyl)azetidinones and related compounds for ring closure>, Quality Control of 617-55-0, the main research area is lankacidin precursor synthesis Stille coupling iodoalkenylazetidinone ring closure; stereoselective acylation azetidinone lankacidin intermediate preparation; selective cleavage silyl azetidinone lankacidin intermediate preparation; regioselective monodeprotection silyl ether.
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 undergo a Stille coupling reaction with a 3-hydroxy-1-(tributylstannyl)hepta-1,5-diene to give an acceptable yield of the corresponding conjugated diene; but the analogous reaction with a 3-tert-butyldimethylsilyloxy-1-(tributylstannyl)hepta-1,5-diene was unsuccessful. A series of 4-[(E)-2-iodoprop-1-enyl]azetidinones, a ring-opened ester and a lactone were also found to undergo Stille reactions with 3-tributylstannylprop-2-enol albeit with variable yields. Asym. syntheses of Me (2R,3R,5S)-3-tert-butyldimethylsilyloxy-2-methyl-5-(2-trimethylsilylethoxy)methoxy-6-oxohexanoate, (3R,4S)-1-tert-butyldimethylsilyl-4-[(E)-2-iodoprop-1-enyl]-3-methylazetidin-2-one, and (5S,2E,6E)-5-tert-butyldimethylsilyloxy-2-methyl-1-phenylsulfonyl-7-tributylstannylhepta-2,6-diene and their incorporation into macrocyclic precursors of the lankacidins were then investigated. Key reactions were a Julia reaction between the aldehyde and the sulfone to form the 12,13-double-bond, a stereoselective acylation of the azetidinone, and formation of macrocycles using intramol. Stille reactions in the presence of a free hydroxyl group at C(8) (lankacidin numbering).
Tetrahedron published new progress about Acylation, stereoselective. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Quality Control of 617-55-0.
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