Biomedical subjects
Publications and source records attributed to John Montgomery.
The direct cyclization of allenyl aldehydes with organozincs in the presence of Ni(COD)(2) provides synthetically versatile homoallylic alcohols. Both monosubstituted and 1,3-disubstituted allenes participate in the process, with the latter allowing preparation of stereochemically defined trisubstituted alkenes. [reaction: see text]
An enantioselective total synthesis of (+)-testudinariol A was completed. A new nickel-catalyzed allenyl aldehyde cyclization was developed in the approach. In addition, an asymmetric anti aldol reaction and a two-directional oxocarbenium ion/vinyl silane condensation were employed as key steps.
[reaction: see text] 1,3-Dienes were prepared by a variety of nickel-catalyzed couplings and cyclization processes. Intermolecular or partially intramolecular couplings of alkynes, vinylzirconium reagents, and either aldehydes or enones efficiently proceeded to generate a broad range of functionalized dienes.
A new two-step procedure for the synthesis of cyclohexenols has been developed. A nickel-catalyzed three-component addition of an enal, alkyne, and acetylenic tin affords substituted hept-4-en-6-ynals. The products of this first step then undergo a second nickel-catalyzed reaction with organozincs or organoboranes to afford densely functionalized cyclohexenols. Variation in each of the four components is tolerated to provide access to a wide range of versatile building blocks.
[reaction: see text] The tetracyclic isogeissoschizoid skeleton has been prepared by a novel route that involves the ozonolysis and double reductive amination of a cyclopentene, a nickel-catalyzed cyclization, and a late-stage Fischer indole synthesis.
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