208465-70-7Relevant articles and documents
Total synthesis of (-)-virginiamycin m2: Application of crotylsilanes accessed by enantioselective Rh(II) or Cu(I) promoted carbenoid Si-H insertion
Wu, Jie,Panek, James S.
, p. 9900 - 9918 (2012/03/08)
A stereoselective synthesis of the antibiotic (-)-virginiamycin M 2 is detailed. A convergent strategy was utilized that proceeded in 10 steps (longest linear sequence) from enantioenriched silane (S)-15. This reagent, which was prepared via a Rh(II)- or Cu(I)-catalyzed carbenoid Si-H insertion, was used to introduce the desired olefin geometry and stereocenters of the C1-C5 propionate subunit. A modified Negishi cross-coupling or an efficient alkoxide-directed titanium-mediated alkyne-alkyne reductive coupling strategy was utilized to assemble the trisubstituted (E,-E)-diene. An underutilized late-stage SmI2-mediated macrocyclization was employed to construct the 23-membered macrocycle scaffold of the natural product (Figure presented).
Total synthesis of (-)-virginiamycin M2
Wu, Jie,Panek, James S.
supporting information; experimental part, p. 6165 - 6168 (2010/12/19)
Has a nice ring to it: A concise and modular total synthesis of the naturally occurring antibiotic virginiamycin M2 is described. A Barbier-type cyclization was used to close the 23-membered macrocycle and deliver virginiamycin M2 in 19 steps from a chiral organosilane.
Total synthesis of pristinamycin II(B)
Breuilles,Uguen
, p. 3149 - 3152 (2007/10/03)
An intramolecular Takai reaction of the iodoaldehyde 4a proceeded with a moderate efficiency to give the macrocyclic hydroxy compound 1b, identified to an authentic sample.
