Synthetic Approach to the ABCD Ring System of Anticancer Agent Fredericamycin A via Claisen Rearrangement and Ring-Closing Metathesis as Key Steps
journal contributionposted on 14.10.2019, 08:29 by Sambasivarao Kotha, Subba Rao Cheekatla, Ambareen Fatma
A new synthetic strategy to the ABCD ring system of the anticancer agent fredericamycin A (NSC-305263) was realized by the Diels–Alder reaction and olefin metathesis as key steps. The tactics developed here for the construction of the ABCD ring system also involve double Claisen rearrangement followed by a retro-Diels–Alder reaction and ring-closing metathesis. The metathesis approach performs a key role in the construction of A and D rings of the ABCD core unit. More importantly, ABCD fragment synthesis was accomplished without the involvement of protecting groups.
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ring-closing metathesisolefin metathesismetathesis approachClaisen rearrangementD ringsNSCABCD ring systemanticancer agent fredericamycinClaisen RearrangementKey StepsconstructionAnticancer Agent FredericamycinABCD core unitRing-Closing MetathesisABCD Ring SystemABCD fragment synthesisSynthetic Approach