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An approach to anti-HIV-1 active Calophyllum coumarin synthesis: An enantioselective construction of 2,3-dimethyl-4-chromanone ring by quinine-assisted intramolecular Michael-type addition

✍ Scribed by Tsutomu Ishikawa; Yumie Oku; Tomohiro Tanaka; Takuya Kumamoto


Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
211 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis


Quinine effectively catalyzes an intramolecular Michael-type addition of 7-hy&oxy-8tigloylcoumarin to give a diastereoisomeric mixture of the corresponding cyclized coumarin with a 2,3dimethyl-4-chromanone skeleton. Satisfactory enantioseleetivity was observed in a cis-chromanone construction, but not in a trans-one.