Novel rearrangements of macrocyclic trichothecenes
Review articleOpen access
1990/01/01 Full-length article DOI: 10.1016/S0040-4039(00)97632-9
Journal: Tetrahedron Letters
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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