Publication: Concise synthesis and confirmation of the absolute configurations of naturally occurring bioactive 2,7′-cyclolignans
Issued Date
2021-03-02
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ISSN
18733581
00404039
00404039
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2-s2.0-85100531346
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Mahidol University
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SCOPUS
Bibliographic Citation
Tetrahedron Letters. Vol.66, (2021)
Suggested Citation
Nannaphat Chumsri, Chutima Kuhakarn, Pawaret Leowanawat, Vichai Reutrakul, Darunee Soorukram Concise synthesis and confirmation of the absolute configurations of naturally occurring bioactive 2,7′-cyclolignans. Tetrahedron Letters. Vol.66, (2021). doi:10.1016/j.tetlet.2021.152827 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/76251
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Title
Concise synthesis and confirmation of the absolute configurations of naturally occurring bioactive 2,7′-cyclolignans
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Abstract
A concise asymmetric synthesis of naturally occurring bioactive 2,7′-cyclolignans, namely 4,4′-dihydroxy-3′,5,5′-trimethoxy-2,7′-cyclolignan and 4,4′-dihydroxy-3,3′,5-trimethoxy-2,7′-cyclolignan, possessing the uncommon 8,8′-syn dimethyl stereochemistry and unsymmetrical C-6 units with 7′,8′-anti-orientation is described using a substrate-controlled stereoselective Friedel-Crafts cyclization as the key step. The products were obtained in good yields with high stereoselectivity. The absolute configurations of natural 4,4′-dihydroxy-3′,5,5′-trimethoxy-2,7′-cyclolignan and those of natural 4,4′-dihydroxy-3,3′,5-trimethoxy-2,7′-cyclolignan were assigned as (7′S,8S,8′S) and (7′R,8R,8′R), respectively, based on the experimental circular dichroism (CD) spectra of the corresponding synthesized compounds.