Novel rearrangements of macrocyclic trichothecenes
Review articleOpen access
Abstract:

AbstractMyrotoxin B (1) readily undergoes electrophilic addition of water and BrOH to give myrotoxin B hydrate (5) and the bromohydrin 2, respectively. When these hemiketals are treated with DBU in THF, they undergo novel rearrangements apparently via their open chain hydroxyketone forms. Myrotoxin B hydrate (5) gives a spirocyclic ketal 6 which is only slightly less cytoxic than 5, even though the macrocyclic ring system has undergone substantial alteration.

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