First total synthesis of a natural product containing a chiral, beta-diketone: synthesis and stereochemical reassignment of siphonarienedione and siphonarienolone.
The first total syntheses of siphonarienolone and siphonarienedione are described. The development of a stereoselective synthesis of beta-diketones facilitated the synthesis of the latter compound. The synthesis of the structures proposed for the natural products afforded compounds whose spectral data did not match those of the natural products. However, the synthesis of compounds isomeric to the proposed structures at C(4) and C(5) afforded compounds identical to the natural products, thereby reassigning the stereochemistry of the natural products.
Calter
Michael A
MA
Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, USA. alter@chem.rochester.edu
Liao
Wensheng
W
D000473:Alkanes / Q000138:chemical synthesis*; D001685:Biological Factors / Q000138:chemical synthesis*; D007659:Ketones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000473:Alkanes; D001685:Biological Factors; D007659:Ketones; C470332:siphonarienedione; C470331:siphonarienolone