Enantioselective total synthesis of isishippuric acid B via intramolecular Michael reaction.
The first enantioselective total synthesis of isishippuric acid B bearing a novel 4,5-seco-6-norquadrane skeleton was accomplished from (R)-citronellal with use of a Diels-Alder cycloaddition and an intramolecular Michael addition as the ring-forming steps. Comparison of the optical rotation of the synthetic material with that of the natural product confirmed the absolute configuration of isishippuric acid B to be 1R, 2R, 8R, and 11R.
Torihata
Munefumi
M
Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Aoba-ku, Sendai 981-8555, Japan.
Nakahata
Takashi
T
Kuwahara
Shigefumi
S
D000818:Animals; D037421:Anthozoa / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000378:metabolism; D003998:Dicarboxylic Acids / Q000138:chemical synthesis*; D015394:Molecular Structure
D000970:Antineoplastic Agents; D003998:Dicarboxylic Acids; C522227:isishippuric acid B