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Concise synthesis and confirmation of the absolute configurations of naturally occurring bioactive 2,7′-cyclolignans

Tetrahedron Letters, ISSN: 0040-4039, Vol: 66, Page: 152827
2021
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Article Description

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,8 S,8′ S ) and (7′ R,8 R,8′ R ), respectively, based on the experimental circular dichroism (CD) spectra of the corresponding synthesized compounds.

Bibliographic Details

Nannaphat Chumsri; Chutima Kuhakarn; Pawaret Leowanawat; Vichai Reutrakul; Darunee Soorukram

Elsevier BV

Biochemistry, Genetics and Molecular Biology; Pharmacology, Toxicology and Pharmaceutics; Chemistry

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