The instability toward Bergman cyclization–reduction decomposition pathways poses a major threat to any proposed synthesis of enediynes.
Myers and co-workers addressed this liability by late-stage dehydrative installation of the olefin.
Without this unsaturation linking the two alkynyl bridges, synthetic intermediates are not disposed toward Bergman-type decomposition, and risk of decomposition is mitigated.
In this case, dehydration of a propargylic alcohol was induced by treatment with Martin sulfurane.
The instability toward Bergman cyclization–reduction decomposition pathways poses a major threat to any proposed synthesis of enediynes. Myers and co-workers addressed this liability by late-stage dehydrative installation of the olefin. Without this unsaturation linking the two alkynyl bridges, synthetic intermediates are not disposed toward Bergman-type decomposition, and risk of decomposition is mitigated. In this case, dehydration of a propargylic alcohol was induced by treatment with Martin sulfurane.
Kedarcidin