91604-66-9Relevant academic research and scientific papers
STEREOCONTROLLED FUNCTIONALIZATION OF CYCLOHEPTADIENE; AN APPROACH TO TYLOSIN AND CARBOMYCIN B FROM A COMMON INTERMEDIATE
Pearson, Anthony J.,Ray, Tapan
, p. 3111 - 3114 (2007/10/02)
Bromolactonization of the cycloheptadienylacetic acid 1 proceeds with good regio- and stereocontrol and provides 4 which serves as a common intermediate for right hand sections of two macrolide antibiotics, tylosin and carbomycin B.
REGIO- AND STEREOCONTROLLED FUNCTIONALIZATION OF CYCLOHEPTADIENE USING ORGANOIRON AND ORGANOSELENIUM CHEMISTRY.
Pearson,Kole,Ray
, p. 6060 - 6074 (2007/10/02)
Whereas the reactions of tricarbonylcycloheptadienyliron salts with nucleophiles generally occur in low yield giving mixtures of products, the corresponding dicarbonyl(triphenylphosphine) and dicarbonyl(triphenyl phosphite) complexes 8 give high yields of single adducts on reaction with a range of nucleophiles. The regioselectivity of nucleophile addition to 8 is strongly dependent on the nucleophile, 'soft' nucleophiles attacking C-1, 'hard' nucleophiles attacking C-2 of the dienyl ligand. The diene complexes 10 resulting from C-1 addition can be reactivated by hydride abstraction with Ph//3C** plus PF//6** minus , to give dienyl complexes 11, which undergo a second nucleophile addition regio- and stereospecifically (trans to the Fe(CO)//2L group). Decomplexation is easily accomplished, leading to cycloheptadienylacetic acid derivatives.
CONJUGATE PHENYLSELENOLACTONIZATION COUPLED WITH ALLYLIC SELENOXIDE REARRANGEMENT FOR FUNCTIONALIZING DIENYLACETIC ACIDS
Pearson, Anthony J.,Ray, Tapan,Richards, Ian C.,Clardy, Jon,Silveira, Linda
, p. 5827 - 5830 (2007/10/02)
Use of the title reactions for the regioselective, and stereoselective functionalization of a range of dienylacetic acids, available from simple organoiron chemistry, is presented.
