The total synthesis of swinholide A. Part 4: Synthesis of swinholide A and isoswinholide A from the protected monomeric seco acid, pre-swinholide A
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Add time:09/02/2019 Source:sciencedirect.com
Swinholide A and isoswinholide A were synthesised in 7 steps from the fully protected seco acid 4. Key steps include: (i) bimolecular acylation, 7 + 10 → 12, (ii) selective hydrolysis of the methyl ester, 16 → 17, and (iii) regioselective macrolactonisation. 17 → 18. The monomeric lactone analogues 2 and 5 were prepared by regioselective macrolactonisation of the seco acid 6, where the ring size was controlled by variation of the reaction conditions.
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