Stereoselective synthesis of eight-membered cyclic ethers by tandem Nicholas reaction/ring-closing metathesis: a short synthesis of (+)-cis-Lauthisan |
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Authors: | Ortega Nuria Martín Tomás Martín Víctor S |
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Institution: | Instituto Universitario de Bioorgánica Antonio González, Universidad de La Laguna, Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Canary Islands, Spain. |
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Abstract: | STRUCTURE: SEE TEXT] Cis-2,8-disubstituted oxocanes and the parent unsaturated precursors were prepared from the corresponding Co2(CO)6-cycloalkynic ethers. Key steps in such synthesis were the ether linkage formation by intermolecular Nicholas reaction, RCM of the suitable acyclic dienyl ether and montmorillonite K-10 induced isomerization of the complexed cycloalkyne. A short synthesis of (+)-cis-lauthisan taking advantage of the developed methodology is described. |
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