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Chiral 7-Oxabicyclo[2.2.1]heptane Building Blocks for Prostanoids

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Abstract

Methyl (Z)-3-[(2R,3R,4S,5S)-5-(2-methoxy-2-oxoethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran-2-yl]-prop-2-enoate was synthesized, and its intramolecular carbocyclization was studied. This reaction proceeds smoothly and quickly under the action of t-BuOK in THF, leading to three cycles with the methoxy and methoxycarbonylmethyl side substituents trans to each other. A stepwise route for the formation of methyl (1R,2R,6S,7R,8R,9R)-9-(2-methoxy-2-oxoethyl)-4,4-dimethyl-3,5,10-trioxatricyclo[5,2,1,02,6]decane-8-carboxylate and methyl (1R,2R,6S,7R,8S,9S)-9-(2-methoxy-2-oxoethyl)-4,4-dimethyl-3.5,10-trioxatricyclo-[5,2,1,02,6]decane-8-carboxylate with the trans orientation of the side substituents is proposed. The observed stereochemical result of the reaction is interpreted in terms of epimerization in the C1 and C4 centers of methyl (Z)-3-[(2R,3R,4S,5S)-5-(2-methoxy-2-oxoethyl)-3,4-(isopropylidenedioxy)-tetrahydrofuran-2-yl]prop-2-enoate, which ultimately leads to the cyclized β,β’-cis diastereomer of methyl (Z)-3-[(2R,3R,4S,5S)-5-(2-methoxy-2-oxoethyl)-3,4-(isopropylidenedioxy)-tetrahydrofuran-2-yl]prop-2-enoate and the corresponding α,α’-cis diastereomer, a precursor of methyl (1R,2R,6S,7R,8S,9S)-9-(2-methoxy-2-oxoethyl)-4,4-dimethyl-3,5,10-trioxatricyclo[5,2,1,02,6]decane-8-carboxylate.

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Acknowledgments

Analytical measurements were performed using the equipment of the Khimiya Center for Collective Use, Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences.

Funding

The work was performed by State order (contact no. AAAA-A17-117011910032-4).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, pr. Oktyabrya 69, Ufa, Republic of Bashkortostan, 450054, Russia

    Z. R. Valiullina, N. A. Ivanova & M. S. Miftakhov

  2. Ufa State Petroleum Technological University, ul. Kosmonavtov 1, Ufa, Republic of Bashkortostan, 450062, Russia

    O. V. Shitikova

Authors
  1. Z. R. Valiullina
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  2. N. A. Ivanova
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  3. O. V. Shitikova
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  4. M. S. Miftakhov
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Corresponding authors

Correspondence to O. V. Shitikova or M. S. Miftakhov.

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Conflict of Interest

The authors declare no conflict of interest.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 8, pp. 1223–1228.

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Valiullina, Z.R., Ivanova, N.A., Shitikova, O.V. et al. Chiral 7-Oxabicyclo[2.2.1]heptane Building Blocks for Prostanoids. Russ J Org Chem 55, 1131–1135 (2019). https://doi.org/10.1134/S1070428019080116

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  • DOI: https://doi.org/10.1134/S1070428019080116

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