Enzymatic Resolution of (.+-.)-5-Acetoxy-4-aryl-(2E)-pentenoate Derivatives

Tanikawa, Shin; Ono, Masahiro; Akita, Hiroyuki

doi:10.1248/cpb.53.565

Cited by 5 publications

(3 citation statements)

References 16 publications

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“…Primary alcohol (−)-45 Lipases can catalyze chemical transformations in both a stereoselective and regioselective fashion. Both kinds of selectivity were exploited for the resolution of 5-acetoxy-4-aryl-(2E)-pentenoate derivatives [42]. These substrates contain a primary alcohol acetate and a α,β-unsaturated acid methyl ester.…”

Section: Primary Alcoholsmentioning

confidence: 99%

Stereoselective Synthesis of Terpenoids through Lipase-Mediated Resolution Approaches

Serra¹,

Simeis²

2020

Catalysts

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This review article focuses on the scientific developments concerning the lipase-mediated synthesis of terpenoids that have been reported in the literature during the last twenty years. More specifically, this review describes in depth the resolution approaches that allow the preparation of the chiral building blocks used for the stereoselective synthesis of bioactive terpenoids. The synthetic methods that have given new and innovative perspectives from a scientific standpoint, and the preparative approaches that possess industrial importance, are described thoroughly.

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Section: Primary Alcoholsmentioning

confidence: 99%

Stereoselective Synthesis of Terpenoids through Lipase-Mediated Resolution Approaches

Serra¹,

Simeis²

2020

Catalysts

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“…Demethylation of 6 under alkaline conditions [22] then afforded the dihydroxy intermediate, which unfortunately could not be auto‐oxidized in air to its corresponding ortho ‐quinone. Instead, this dihydroxy phenol intermediate was treated with MnO 2 , generating the para ‐quinone methide 6 a , which was directly subjected to Wacker oxidation [23] without further purification, eventually affording synthetic cryptotrione ( 1 ) in 40 % yield. Moreover, subjection of alkene 24 to the similar aforementioned procedures from alkene 23 to cryptotrione ( 1 ), 7′‐ epi ‐cryptotrione ( 25 ) was successfully achieved in 18 % yield over 5 steps.…”

Section: Figurementioning

confidence: 99%

Total Synthesis of Cryptotrione

Lyu

Zhong

et al. 2020

Angewandte Chemie

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The total synthesis of cryptotrione (1) was enabled by substrate-controlled diastereoselective construction of the bicyclo[3.1.0]hexene framework through platinum-catalyzed enyne cycloisomerization and Lewis acid induced polyene cyclization to construct the abietane-type tricyclic diterpene skeleton. The stereogenic tertiary carbon center in the side chain was installed in a diastereodivergent manner by conjugate addition reactions.

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“…Lipase OF-360 from Candida rugosa was selected in order to accomplish the resolution of substituted (±)-5-acetoxy-4-aryl-(2E)pentenoates [61] (Figure 12) through the hydrolysis of the acetate ester functional group. By means of this enzymatic transformation compounds of type 70 were obtained in high enantiomeric purity and were transformed into the phenolic sesquiterpenes (R)-elvirol (71) [62] and (S)-curcudiol (67) [63].…”

Section: Serramentioning

confidence: 99%

Enzyme-Mediated Synthesis of Sesquiterpenes

Serra

2015

Natural Product Communications

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This review article focuses mainly on the scientific developments concerning the enzyme-mediated synthesis of sesquiterpenes which have been reported in the academic and patent literature during the last twenty years. Nevertheless, this is not a comprehensive description of every single biotransformation involving sesquiterpenes. Only synthetic approaches that have represented a new and innovative perspective from a scientific standpoint are reported. More specifically, the review describes in depth how the use of metabolic engineering of the microbial biotransformations and of the isolated enzymes were exploited in order to perform chemo-and stereoselective chemical transformations of interest for sesquiterpenes synthesis.

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Enzymatic Resolution of (.+-.)-5-Acetoxy-4-aryl-(2E)-pentenoate Derivatives

Cited by 5 publications

References 16 publications

Stereoselective Synthesis of Terpenoids through Lipase-Mediated Resolution Approaches

Stereoselective Synthesis of Terpenoids through Lipase-Mediated Resolution Approaches

Total Synthesis of Cryptotrione

Enzyme-Mediated Synthesis of Sesquiterpenes

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