Step-Economic Total Synthesis of Melosatin A from Eugenol.
ACS Omega
; 8(25): 23174-23181, 2023 Jun 27.
Article
em En
| MEDLINE
| ID: mdl-37396254
ABSTRACT
An efficient and straightforward route toward the isatin-type natural product melosatin A is reported, employing a trisubstituted aniline as a key intermediate. The latter was synthesized in 4 steps and 60% overall yield from eugenol, through its regioselective nitration, sequentially followed by a Williamson methylation, an olefin cross-metathesis with 4-phenyl-1-butene and the simultaneous reduction of olefin and nitro groups. The final step, a Martinet cyclocondensation of the key aniline with diethyl 2-ketomalonate, provided the natural product with 68% yield.
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MEDLINE
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En
Ano de publicação:
2023
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Article