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The Total Synthesis of (−)‐Amathaspiramide F
Author(s) -
Hughes Chambers C.,
Trauner Dirk
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20021202)41:23<4556::aid-anie4556>3.0.co;2-e
Subject(s) - chirality (physics) , sequence (biology) , proline , retrosynthetic analysis , polar , regeneration (biology) , scheme (mathematics) , stereochemistry , chemistry , physics , mathematics , biology , total synthesis , amino acid , particle physics , biochemistry , quantum mechanics , genetics , symmetry breaking , mathematical analysis , chiral symmetry breaking , nambu–jona lasinio model
Breaking the cis rule : L ‐Proline and not as expected D ‐proline led to (−)‐amathaspiramide F with the correct configuration in a short sequence of steps (see retrosynthetic scheme). This synthesis features an exception to the principle of self‐regeneration of chirality and a strategy for circumventing a problematic Nef reaction in the presence of densely spaced polar functionality.