Total Synthesis and Structural Assignment of (-)-Fusaequisin A.
(-)-Fusaequisin A is an irregularly assembled polyketide isolated from the ascomycete Fusarium equiseti. Fusaequisin A shares a carbon backbone with curvicollide C from the ascomycete Podospora curvicolla but its absolute configuration remained hitherto unsettled. Herein, we document the total synthesis of (-)-fusaequisin A and its 4-O-desmethyl derivative following a central-to-lateral building block strategy. Catalytic asymmetric Claisen rearrangement, Julia-Kocienski olefination and olefin cross-metathesis served as key C/C-connecting transformations. The constitution and absolute configuration of (-)-fusaequisin A was deduced and the original structural assignment was adjusted.
['Schmidt|Ann-Christin|AC|', 'Hiersemann|Martin|M|http://orcid.org/0000-0003-4743-5733']
total synthesis polyketides asymmetric synthesis natural products structural elucidation