Co2(CO)8-mediated endo mode cyclization of epoxy-alcohol: synthesis of 2-ethynyl-3-hydroxy-2-methyltetrahydropyran and 2-ethynyl-3-hydroxy-3-methyltetrahydropyran derivatives.

@article{Mukai2001Co2CO8mediatedEM,
  title={Co2(CO)8-mediated endo mode cyclization of epoxy-alcohol: synthesis of 2-ethynyl-3-hydroxy-2-methyltetrahydropyran and 2-ethynyl-3-hydroxy-3-methyltetrahydropyran derivatives.},
  author={C. Mukai and S. Yamaguchi and I. J. Kim and M. Hanaoka},
  journal={Chemical \& pharmaceutical bulletin},
  year={2001},
  volume={49 5},
  pages={
          613-8
        }
}
Successive treatment of 4,5-epoxy-5-methyl-7-trimethylsilyl-6-heptyne-1-ol with Co2(CO)8 at 0 degrees C and a catalytic amount of BF3 x OEt2 at -78 degrees C gave the tetrahydropyran derivatives with the cobalt-complexed moiety. Similarly 4,5-epoxy-4-methyl-7-trimethylsilyl-6-heptyne-1-ol underwent ring closure under the above conditions to provide the corresponding tetrahydropyran derivatives. The preferential endo mode cyclization over the exo one was observed in these experiments. 
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9 Citations

9 Citations

Citation Type

Citation Type

Cyclopropanes in Nicholas reaction: formation of spiroketals with a five-membered and a seven- or an eight-membered ring
A new entry to oxacycles via base-catalyzed endo mode cyclization of allenyl sulfoxides and sulfones.
Synthesis of oxaspiro[m.n] skeletons based on the nicholas reaction
Chapter 7 First total synthesis of several natural products based on alkyne-Co2(CO)6 complexes
An Approach to Cyclic α-Amino Acids by a Novel Hetero Diels-Alder/Intramolecular Hydantoin Enolate Alkylation Strategy: An Approach to Halichlorine
[Development of highly selective reactions based on metal carbonyls and its application to synthesis of bioactive compounds].
  • C. Mukai
  • Chemistry, Medicine
  • Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan
  • 2002
Epoxide-opening cascades in the synthesis of polycyclic polyether natural products.
Epoxidöffnungskaskaden zur Synthese polycyclischer Polyether-Naturstoffe
Co2(CO)8‐Mediated endo Mode Cyclization of Epoxy‐Alcohol: Synthesis of 2‐Ethynyl‐3‐hydroxy‐2‐methyltetrahydropyran and 2‐Ethynyl‐3‐hydroxy‐3‐methyltetrahydropyran Derivatives.

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