Stereocontrolled Synthesis of (−)-Galanthamine

Satcharoen, Vachiraporn; McLean, Neville; Kemp, Stephen C.; Camp, Nicholas P.; Brown, Richard C. D.

doi:10.1021/ol070255i

Cited by 92 publications

(34 citation statements)

References 19 publications

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“…in toluene upon heating at reflux to give the desired product 9 along with the over‐reduced compound 10 in a ratio of 4:1. The intermediate 9 was successfully converted to the known compound 11 , thus completing a formal synthesis of (+)‐galanthamine.…”

Section: Figurementioning

confidence: 99%

Chemoenzymatic Total Synthesis of (+)‐Galanthamine and (+)‐Narwedine from Phenethyl Acetate

Endoma‐Arias

Hudlický

2016

Chemistry A European J

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The stereoselective total synthesis of unnatural (+)-galanthamine starting from phenethyl acetate is described. Chirality was introduced via microbial dihydroxylation of phenethyl acetate with the recombinant strain JM109 (pDTG601A) to the corresponding cis-cyclohexadi-enediol, configuration of which provided the absolute stereochemistry of the ring C of (+)-galanthamine. Intramolecular Heck cyclization was used to form the quaternary carbon and dibenzofuran functionality. The synthesis of (+)-galanthamine was completed in a total of ten steps and an overall yield of 5.5 %. Experimental and spectral data are provided for all new compounds.

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Section: Figurementioning

confidence: 99%

Chemoenzymatic Total Synthesis of (+)‐Galanthamine and (+)‐Narwedine from Phenethyl Acetate

Endoma‐Arias

Hudlický

2016

Chemistry A European J

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“…Hydroboration of the terminal alkene of 77 followed by oxidation gave homoallylic alcohol 78 in excellent yield, and palladium-catalyzed cyclization followed by SeO 2 oxidation gave 79 . Mesylation of 79 followed by deprotection afforded (-)-galanthamine [71]. …”

Section: Ring-closing Enyne Metathesis (Rcm)mentioning

confidence: 99%

Recent Progress on Enyne Metathesis: Its Application to Syntheses of Natural Products and Related Compounds

Mori

2010

Materials

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Olefin metathesis using ruthenium carbene complexes is a useful method in synthetic organic chemistry. Enyne metathesis is also catalyzed by these complexes and various carbo- and heterocycles could be synthesized from the corresponding enynes. Dienyne metathesis, cross enyne metathesis and ring-opening enyne metathesis have been further developed. Various complicated compounds, such as the natural products and the related biologically active substances, could be synthesized using these metatheses reactions. Skeletal reorganization using the transition metals and metallotropic rearrangement are also discussed.

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“…Its preparation has been realized starting from isovanillin. 63 The Heck reaction offered a convenient and ingenious way for the formation of three of the four rings of galanthamine.…”

Section: Silver As a Halogen Scavengermentioning

confidence: 99%