Applications of NHC-mediated O- to C-carboxyl transfer: synthesis of (±)-N-benzyl-coerulescine and (±)-horsfiline

Thomson, Jennifer E.; Kyle, Andrew F.; Ling, Kenneth B.; Smith, S.M.; Slawin, Alexandra M. Z.; Smith, Andrew D.

doi:10.1016/j.tet.2010.03.047

Cited by 36 publications

(13 citation statements)

References 62 publications

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“…Column chromatography was performed on Spectrochem India silica gel (60–120 mesh) using mixture of ethyl acetate and hexane as eluent. All the rac ‐alcohol substrates ( 1a – 1t ) and rac ‐ 3a – 3t were prepared as previously reported 60–65 . For detailed synthetic procedures, see the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

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Candida antarctica lipase‐B‐catalyzed kinetic resolution of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles

Kumar

Sahoo

et al. 2020

Chirality

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Candida antarctica (CAL-B) lipase-catalyzed resolution of 1,3-dialkyl-3hydroxymethyl oxindoles has been performed to obtain (R)-1,3-dialkyl-3acetoxymethyl oxindoles with up to 99% ee and (S)-1,3-dialkyl-3-hydroxymethyl oxindoles with up to 78% ee using vinyl acetate as acylating agent and acetonitrile as solvent transforming (S)-3-allyl-3-hydroxymethyl oxindole to (3S)-1 0-benzyl-5-(iodomethyl)-4,5-dihydro-2H-spiro[furan-3,3 0-indolin]-2 0-one. The optically active 3-substituted-3-hydroxymethyl oxindoles and spirooxindoles are among the key synthons in the synthesis of potentially biologically active molecules.

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Section: Methodsmentioning

confidence: 99%

“…All the rac-alcohol substrates (1a-1t) and rac-3a-3t were prepared as previously reported. [60][61][62][63][64][65] F I G U R E 1 Some biologically important 3,3-disubstituted oxindole For detailed synthetic procedures, see the Supporting Information.…”

Section: Chemicalsmentioning

confidence: 99%

Candida antarctica lipase‐B‐catalyzed kinetic resolution of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles

Kumar

Sahoo

et al. 2020

Chirality

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“…( R )‐ tert ‐Butyl 3‐(5‐methoxy‐2‐nitrophenyl)‐1‐methylpyrrolidine‐3‐carboxylate (11) : Compound 16 (199 mg, 0.4 mmol) was dissolved in methylamine solution (33 wt % in absolute ethanol (10 mL) 4k. At room temperature, the reaction mixture was stirred for 48 h. After all of solvent was removed in vacuo, the residue was purified by column chromatography (silica gel, hexane/EtOAc/acetone/methanol=10:16:4:1) to afford 11 (313.5 mg, 93 % yield) as a yellow solid.…”

Section: Methodsmentioning

confidence: 99%

Efficient Enantioselective Total Synthesis of (−)‐Horsfiline

Hong

Jung

Park

et al. 2013

Chemistry A European J

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A new efficient and concise enantioselective synthetic method for (-)-horsfiline is reported. (-)-Horsfiline could be obtained from diphenylmethyl tert-butyl malonate in 9 steps (32%,>99% ee) by using the enantioselective phase-transfer catalytic allylation (91% ee) as the key step. This approach can be applied as a practical route for the large-scale synthesis of spirooxindole natural products, which enables a systematic investigation of their biological activity to be performed.

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“…Smith and co‐workers have accomplished the synthesis of alkaloids belonging to this class [e.g., (±)‐coerulescine and (±)‐horsfiline] via 1 as a key intermediate . The challenge of synthesizing 2‐oxindoles containing an all‐carbon quaternary centre at the C‐3 position continues to inspire ingenious solutions for bond formation.…”

Section: Introductionmentioning

confidence: 99%

Unified Approach to Fused and Spirocyclic Oxindoles through Lewis‐Acid‐Promoted Opening of Spiroepoxyoxindoles with Allylsilanes: Application to the Formal Synthesis of (±)‐Physovenine

et al. 2017

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A protocol for the construction of oxindoles containing all‐carbon quaternary centres in a highly regioselective manner has been developed. The reaction involves opening of spiroepoxyoxindoles with allylsilanes to give Hosomi–Sakurai‐type products as well as new silicon‐containing spirocyclic oxindoles. A formal synthesis of (±)‐physovenine was accomplished in five steps using this protocol.

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Applications of NHC-mediated O- to C-carboxyl transfer: synthesis of (±)-N-benzyl-coerulescine and (±)-horsfiline

Cited by 36 publications

References 62 publications

Candida antarctica lipase‐B‐catalyzed kinetic resolution of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles

Candida antarctica lipase‐B‐catalyzed kinetic resolution of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles

Efficient Enantioselective Total Synthesis of (−)‐Horsfiline

Unified Approach to Fused and Spirocyclic Oxindoles through Lewis‐Acid‐Promoted Opening of Spiroepoxyoxindoles with Allylsilanes: Application to the Formal Synthesis of (±)‐Physovenine

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