ChemInform Abstract: Synthesis of Sulfur-Containing Olefinic Peptide Mimetic Farnesyl Transferase...
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1999 amino acids, peptides amino acids, peptides U 0400 28 - 225 Synthesis of Sulfur-Containing Olefinic Peptide Mimetic Farnesyl Transferase Inhibitors Using the Nozaki–Hiyama–Kishi Reaction and Cuprate S N 2’ Displacements. — Two iterative Nozaki–Hiyama–Kishi (NHK) and cuprate S N 2’ reactions are applied to construct the two double bonds in the target aminothiol inhibitors B956 (XVI) and B957 (XVII). Normal syn NHK reaction and substrate-dependent syn and anti-S N 2’ diastereoselectivities accompanied by exclusive (E)-olefin selectivity are observed for the first iteration (I) → (V) (diastereoselectivity is determined by later DIBAL reduction). The second iteration proceeds with unexpected epimerization and a strong preference for syn diastereoselectivity in the NHK reaction (VIII) → (IX) + (X), while an unusual (Z)-olefin is observed for the S N 2’ reaction (XII) → (XIV). — (YANG, HU; SHENG, XIAONING C.; HARRINGTON, EDMUND M.; ACKERMANN, KAREN; GARCIA, ANA MARIA; LEWIS, MICHAEL D.; J. Org. Chem. 64 (1999) 1, 242-251; Eisai Res. Inst., Andover, MA 01810, USA; EN) 1
Transcript of ChemInform Abstract: Synthesis of Sulfur-Containing Olefinic Peptide Mimetic Farnesyl Transferase...
1999 amino acids, peptides
amino acids, peptidesU 0400
28 - 225Synthesis of Sulfur-Containing Olefinic Peptide Mimetic FarnesylTransferase Inhibitors Using the Nozaki–Hiyama–Kishi Reaction andCuprate SN2’ Displacements. — Two iterative Nozaki–Hiyama–Kishi(NHK) and cuprate SN2’ reactions are applied to construct the two double bondsin the target aminothiol inhibitors B956 (XVI) and B957 (XVII). Normal synNHK reaction and substrate-dependent syn and anti-SN2’ diastereoselectivitiesaccompanied by exclusive (E)-olefin selectivity are observed for the first iteration(I) → (V) (diastereoselectivity is determined by later DIBAL reduction). Thesecond iteration proceeds with unexpected epimerization and a strong preferencefor syn diastereoselectivity in the NHK reaction (VIII) → (IX) + (X), while anunusual (Z)-olefin is observed for the SN2’ reaction (XII)→ (XIV). — (YANG,HU; SHENG, XIAONING C.; HARRINGTON, EDMUND M.; ACKERMANN,KAREN; GARCIA, ANA MARIA; LEWIS, MICHAEL D.; J. Org. Chem. 64(1999) 1, 242-251; Eisai Res. Inst., Andover, MA 01810, USA; EN)
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1999 amino acids, peptides
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