Synthesis of 8-oxoprotoberberines using acid-mediated cyclization or the Heck reaction

Chen, Anfeng; Zhao, Kun; Zhang, Hankun; Gan, Xianwen; Lei, Min; Hu, Lihong

doi:10.1007/s00706-011-0656-6

Cited by 9 publications

(1 citation statement)

References 35 publications

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“…In order to demonstrate the synthetic usefulness of our cascade reaction, we applied it to the synthesis of the alkaloid 8-oxypseudopalmatine. Previous methods to synthesize this compound, which is found naturally in Stephama suberosa Forman ( Menispermaceae ), , require complicated starting materials , and lengthy sequences with low overall yields . To use our approach, we first transformed the commercially available bromide 5 into alkynol 1b in 94% yield, which was then reacted with the commercially available imine 2b in DMSO with 20% mol t -BuOK as the catalyst.…”

Section: Resultsmentioning

confidence: 99%

Transition Metal-Free Cascade Reactions of Alkynols to Afford Isoquinolin-1(2H)-one and Dihydroisobenzofuran Derivatives

Shi

Mao

et al. 2014

J. Org. Chem.

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Transition metal-free cascade reactions of alkynols with imines have been achieved using potassium tert-butoxide as catalyst. Switching the reaction solvent gives two kinds of products in good yield: isoquinolin-1(2H)-one derivatives and dihydroisobenzofuran derivatives. This approach was used to generate the natural product 8-oxypseudopalmatine in a two-step procedure from commercially available starting materials. Additionally, multicomponent reactions of alkynols, aldehydes, and amines were also successfully achieved to afford isoquinolin-1(2H)-one derivatives.

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