Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 6, Issue 15, Pages 2815-2819Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b806593d
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Deprotonation of o-hydroxybenzyl acetate with (i)PrMgCl provides a method of generating an o-quinone methide under mild, anionic conditions, such that highly sensitive exo-enol ethers can be employed as 2 pi partners in hetero-Diels-Alder reactions. This process results in mono-benzannelated spiroketals such as those found in the natural products berkelic acid, the chaetoquadrins or cephalostatin 6.
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