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Total Synthesis of Nominal Diazonamides—Part 2: On the True Structure and Origin of Natural Isolates
Author(s) -
Li Jing,
Burgett Anthony W. G.,
Esser Lothar,
Amezcua Carlos,
Harran Patrick G.
Publication year - 2001
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(20011217)40:24<4770::aid-anie4770>3.0.co;2-t
Subject(s) - reinterpretation , natural product , natural (archaeology) , stereochemistry , acetal , product (mathematics) , chemistry , mathematics , biology , philosophy , aesthetics , paleontology , geometry
Unable to bear the weight of scrutiny , the original structure proposed for (−)‐diazonamide A ( 1 ) must be revised. A convergent, stereocontrolled total synthesis provided 1 , which shows altered physical and spectroscopic characteristics relative to those of a sample of the natural product. Reinterpretation of reported data and new insight indicate that the actual structure of diazonamide A is the aminal‐containing ( S )‐ α ‐hydroxy isovaleric acid conjugate 2 . Gratifyingly, a synthetic C11 acetal congener of 2 is, by all biological measures examined, similarly potent and functionally equivalent to the antimitotic natural product.