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Rh-Catalyzed Conjugate Addition of Aryl and Alkenyl Boronic Acids to ?-Methylene-?-lactones: Stereoselective Synthesis of trans-3,4-Disubstituted ?-Lactones.

ABSTRACT: A one-step preparation of 3,4-disubstituted ?-lactones through Rh-catalyzed conjugate addition of aryl or alkenyl boronic acids to ?-methylene-?-lactones is described. The operationally simple, stereoselective transformation provides a broad range of ?-lactones from individual ?-methylene-?-lactone templates. This methodology allowed for a direct, final-step C-3 diversification of nocardiolactone, an antimicrobial natural product.

SUBMITTER: Malapit CA

PROVIDER: S-EPMC5834916 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature

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Rh-Catalyzed Conjugate Addition of Aryl and Alkenyl Boronic Acids to α-Methylene-β-lactones: Stereoselective Synthesis of trans-3,4-Disubstituted β-Lactones.

Malapit Christian A CA Luvaga Irungu K IK Caldwell Donald R DR Schipper Nicholas K NK Howell Amy R AR

Organic letters 20170815 17

A one-step preparation of 3,4-disubstituted β-lactones through Rh-catalyzed conjugate addition of aryl or alkenyl boronic acids to α-methylene-β-lactones is described. The operationally simple, stereoselective transformation provides a broad range of β-lactones from individual α-methylene-β-lactone templates. This methodology allowed for a direct, final-step C-3 diversification of nocardiolactone, an antimicrobial natural product. ...[more]

PMID: 28809569

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