Substrate to catalyst dependent conversion of β,γ-dihydroxyesters to butenolides and/or γ-ketoesters: synthesis of heritol, heritonin and mintlactones

Govande, Chitra A.

doi:10.1039/b109544g

Cited by 9 publications

(1 citation statement)

References 9 publications

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“…[39] This natural product exhibits potent piscicidal activity and has been used by local fishermen to kill invasive fish. To date,anumber of synthetic routes have been reported to access 7, [40] however, only two of them are asymmetric,a nd require 9-15 steps. [11a,40h] We proposed that the a-tetralone intermediate (28;S cheme 10) in Chavans synthesis [11a] could be accessed by the CÀC/CÀHc ascade approach in ac onvenient manner,a nd would lead to astreamlined preparation of 7.Following the same procedure of preparing 11,the compound 29 was obtained in 95 %yield and 99 % ee with the [Rh(C 2 H 4 ) 2 Cl] 2 /(R,R)-Ph-bod catalyst system.…”

Section: Angewandte Chemiementioning

confidence: 99%

Asymmetric Total Syntheses of Di‐ and Sesquiterpenoids by Catalytic C−C Activation of Cyclopentanones

et al. 2020

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To show the synthetic utility of the catalytic C−C activation of less strained substrates, described here are the collective and concise syntheses of the natural products (−)‐microthecaline A, (−)‐leubehanol, (+)‐pseudopteroxazole, (+)‐seco‐pseudopteroxazole, pseudopterosin A–F and G—J aglycones, and (+)‐heritonin. The key step in these syntheses involve a Rh‐catalyzed C−C/C−H activation cascade of 3‐arylcyclopentanones, which provides a rapid and enantioselective route to access the polysubstituted tetrahydronaphthalene cores presented in these natural products. Other important features include 1) the direct C−H amination of the tetralone substrate in the synthesis of (−)‐microthecaline A, 2) the use of phosphoric acid to enhance efficiency and regioselectivity for problematic cyclopentanone substrates in the C−C activation reactions, and 3) the direct conversion of serrulatane into amphilectane diterpenes by an allylic cyclodehydrogenation coupling.

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Section: Angewandte Chemiementioning

confidence: 99%

Asymmetric Total Syntheses of Di‐ and Sesquiterpenoids by Catalytic C−C Activation of Cyclopentanones

et al. 2020

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show abstract

Asymmetric Total Syntheses of Di‐ and Sesquiterpenoids by Catalytic C−C Activation of Cyclopentanones

et al. 2020

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To show the synthetic utility of the catalytic C À C activation of less strained substrates,d escribed here are the collective and concise syntheses of the natural products (À)microthecaline A, (À)-leubehanol, (+ +)-pseudopteroxazole, (+ +)-seco-pseudopteroxazole,p seudopterosin A-F and G-J aglycones,a nd (+ +)-heritonin. The key step in these syntheses involve aR h-catalyzed C À C/C À Ha ctivation cascade of 3arylcyclopentanones,w hichp rovides ar apid and enantioselective route to access the polysubstituted tetrahydronaphthalene cores presented in these natural products.Other important features include 1) the direct CÀHa mination of the tetralone substrate in the synthesis of (À)-microthecaline A, 2) the use of phosphoric acid to enhance efficiency and regioselectivity for problematic cyclopentanone substrates in the C À Ca ctivation reactions,a nd 3) the direct conversion of serrulatane into amphilectane diterpenes by an allylic cyclodehydrogenation coupling.

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Synthesis of 2-(5-hydroxymethyl-2-formylpyrrol-1-yl)propionic acid lactone

Liu

et al. 2012

Chem Nat Compd

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Substrate to catalyst dependent conversion of β,γ-dihydroxyesters to butenolides and/or γ-ketoesters: synthesis of heritol, heritonin and mintlactones

Cited by 9 publications

References 9 publications

Asymmetric Total Syntheses of Di‐ and Sesquiterpenoids by Catalytic C−C Activation of Cyclopentanones

Asymmetric Total Syntheses of Di‐ and Sesquiterpenoids by Catalytic C−C Activation of Cyclopentanones

Asymmetric Total Syntheses of Di‐ and Sesquiterpenoids by Catalytic C−C Activation of Cyclopentanones

Synthesis of 2-(5-hydroxymethyl-2-formylpyrrol-1-yl)propionic acid lactone

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