Chapter 8 Diphenyloxazinones: versatile templates for the asymmetric synthesis of α-amino acid, peptide isosteres, and natural products

Abstract

Publisher Summary This chapter shows the diphenyloxazinone template, which possesses a wide variety of reactivity manifolds that provides access to the synthesis of structurally diverse amino acids, their derivatives, and nitrogen-containing natural products. Current methods include glycine electrophilic reactivity, conversion to the phosphonate, enolate alkylation, radical chemistry, azomethine ylide dipolar cycloadditions, formation of heterocycles at nitrogen, and homologation at the lactone carbonyl, which has provided access to peptide isosteres and other nitrogen-containing substances in optically pure form. The chapter also provides guidelines for selecting hydrogenation conditions, but the auxiliary removal procedure remains highly substrate-dependent and necessarily empirical. Current natural products whose syntheses are being pursued include palau’ amine, axinellamine, quinine, tuberostemoninol, MPC-1001, ecteinascidin 743, lemonomycin, renieramycin I, bioxalomycin α2, microsclerodermin H, quinine, nakadomarin A, zetekitoxin, and numerous isotopically labeled amino acids and their derivatives.