Stereoselective synthesis of (-)-acanthoic acid.
[reaction: see text] The first stereoselective synthesis of (-)-acanthoic acid (1) has been designed and accomplished. Our synthetic plan departs from (-) Wieland-Miesher ketone (7) and calls upon a Diels-Alder cycloaddition reaction for the construction of the C ring of 1. The described synthesis confirms the proposed stereochemistry of 1 and represents an efficient entry into an unexplored class of biologically active diterpenes.
Ling
T
T
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.
Kramer
B A
BA
Palladino
M A
MA
Theodorakis
E A
EA
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D007723:Korea; D008968:Molecular Conformation; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism
D000894:Anti-Inflammatory Agents, Non-Steroidal; D004224:Diterpenes; D007202:Indicators and Reagents; C099958:acanthoic acid