73814-79-6Relevant academic research and scientific papers
Total synthesis of scytophycin C. 1. Stereoselective syntheses of the C(1)-C(18) segment and the C(19)-C(31) segment
Nakamura, Ryoichi,Tanino, Keiji,Miyashita, Masaaki
, p. 3579 - 3582 (2007/10/03)
[Equation presented] Stereoselective total synthesis of scytophycin C, a marine 22-membered macrolide displaying potent activity against a variety of human carcinoma cell lines, has been reported in which the polypropionate structure bearing contiguous as
Synthetic Studies on Polypropionate Antibiotics Based on the Stereospecific Methylation of γ,δ-Epoxy Acrylates by Trimethylaluminum. A Highly Stereoselective Construction of the Eight Contiguous Chiral Centers of Ansa-chains of Rifamycins
Miyashita, Masaaki,Yoshihara, Kousei,Kawamine, Katsumi,Hoshino, Masahide,Irie, Hiroshi
, p. 6285 - 6288 (2007/10/02)
A highly stereoselective construction of the eight contiguous chiral centers of ansa-chains of rifamycins has been accomplished by the iterative use of the stereospecific methylation of γ,δ-epoxy acrylates by trimethylaluminum which was recently developed
STEREOSELECTIVE SN2' ADDITIONS OF ORGANOCUPRATES TO HOMOCHIRAL ACYLIC VINYLOXIRANES
Marshall, James A.,Trometer, Joseph D.,Cleary, Darryl G.
, p. 391 - 402 (2007/10/02)
Additions of various methylcopper reagents to the homochiral acylic vinyloxiranes A14, A15, B6-B9, and C5, C6 were performed in order to evaluate E/Z and syn/anti preferences.The unsubstituted oxiranes A14 and A15 gave a mixture of SN2 and SN2' substitution products with the four reagents examined, LiMe2Cu, LiMeCuCN, BrMgMe2Cu, and LiMeCuI*BF3.The more highly substituted systems B6-B9 derived from geraniol and C5, C6 derived from nerol yielded only SN2' products.The (Z)-allylic alcohol derivatives B8 and C6 and LiMeCuCN gave the best anti/syn ratios (99:1 and 97:3, respectively).In both cases the newly formed double bond was exclusively E.
