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


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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.

作者简介

Z. Valiullina

Ufa Institute of Chemistry, Ufa Federal Research Center

Email: bioreg@anrb.ru
俄罗斯联邦, pr. Oktyabrya 69, Ufa, Republic of Bashkortostan, 450054

N. Ivanova

Ufa Institute of Chemistry, Ufa Federal Research Center

Email: bioreg@anrb.ru
俄罗斯联邦, pr. Oktyabrya 69, Ufa, Republic of Bashkortostan, 450054

O. Shitikova

Ufa State Petroleum Technological University

编辑信件的主要联系方式.
Email: ovs11@mail.ru
俄罗斯联邦, ul. Kosmonavtov 1, Ufa, Republic of Bashkortostan, 450062

M. Miftakhov

Ufa Institute of Chemistry, Ufa Federal Research Center

编辑信件的主要联系方式.
Email: bioreg@anrb.ru
俄罗斯联邦, pr. Oktyabrya 69, Ufa, Republic of Bashkortostan, 450054

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