Practical Enzymatic Desymmetrization of 2‐(Ethoxycarbonyl)propane‐1,3‐diyl Dihexanoate and Model Cyclization for the A–D Ring System of Lysergic Acid | Zendy

Miyata Sachiho | Zendy; Kumamoto Takuya | Zendy; Ishikawa Tsutomu | Zendy

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Practical Enzymatic Desymmetrization of 2‐(Ethoxycarbonyl)propane‐1,3‐diyl Dihexanoate and Model Cyclization for the A–D Ring System of Lysergic Acid

Author(s) -

Miyata Sachiho,

Kumamoto Takuya,

Ishikawa Tsutomu

Publication year - 2007

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.200790144

Subject(s) - chemistry , desymmetrization , derivative (finance) , yield (engineering) , ring (chemistry) , stereochemistry , absolute configuration , hydrolysis , propane , lipase , medicinal chemistry , catalysis , organic chemistry , enzyme , enantioselective synthesis , materials science , financial economics , economics , metallurgy

Porcine pancreas lipase‐catalyzed hydrolysis of symmetrical 2‐(ethoxycarbonyl)propane‐1,3‐diyl dihexanoate, under the modified conditions of the Seebach protocol, afforded a desymmetrized monohexanoate in 40–51% yield with 91–94% ee, even in a gram‐scale reaction. The absolute configuration of a half‐hydrolyzed (−)‐product was determined to be ( R ) by conversion to a known 2‐methylpropane‐1,3‐diol derivative. Samarium iodide‐induced radical cyclization of 2‐oxo‐3‐phenylethylamine with a C 4 unit on the N‐atom, derived from the racemic monohexanoate, afforded a 3‐phenylpiperidine derivative as a model construction of the A–D ring system of lysergic acid.

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