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Enantio‐ and Diastereoselective Construction of α,α‐Disubstituted α‐Amino Acids for the Synthesis of Biologically Active Compounds
Author(s) -
Ohfune Yasufumi,
Shinada Tetsuro
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500434
Subject(s) - chemistry , total synthesis , oxazoline , stereochemistry , strecker amino acid synthesis , enantioselective synthesis , alkylation , desymmetrization , nitrene , claisen rearrangement , combinatorial chemistry , organic chemistry , catalysis
Natural and unnatural compounds possessing an α,α‐disubstituted α‐amino acid substructure have received significant attention because of their structural complexity and potent biological activity. Many methods have been developed for the enantio‐ and diastereoselective synthesis of α,α‐disubstituted α‐amino acids, many of which are focused on the total synthesis of natural products and related bioactive compounds. This microreview highlights recent advances in synthetic methods utilized for the synthesis of (1) α‐substituted serine analogs, which were extensively transformed into glutamate and enkephalin analogs, and (2) natural products such as lactacystin, manzacidins, kaitocephalin, altemicidin, sphingofungins, and neooxazolomycin. The key methods for the construction of these higher‐order structures are the asymmetric Strecker synthesis and enolate‐Claisen rearrangements used by our group, and aldol condensation of an enolate or bislactim, mercurio‐ or iodo‐cyclization, alkylation of an oxazoline, rearrangement of a trichloroacetimidate, nitrene insertion into a C–H bond, carbene insertion into a C–N bond, a Diels–Alder reaction, Lewis acid‐induced epoxide opening, and other methods by other groups. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)