Stereoselective synthesis of (R)-(−) and (S)-(+)-phoracantholide I from (R)-(+)-γ-valerolactone

Datrika, Rajender; Kallam, Srinivasa Reddy; Khobare, Sandip R.; Gajare, Vikas; Kommi, Muralikrishna; Mohan, H. Rama; Siddaiah, Vidavalur; Pratap, T. V.

doi:10.1016/j.tetasy.2016.05.008

Cited by 15 publications

(11 citation statements)

References 35 publications

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“…Next, the utility of this methodology was demonstrated by further conversion of chiral GVL (Scheme 9b and c). The chiral GVL could be easily converted to ( R )‐4 and ( S )‐6 , [20, 5b] which are precursors of the P‐Chirogenic PhosPholane ligand and natural product ( S )‐(+)‐phoracantholide I, respectively.…”

Section: Resultsmentioning

confidence: 99%

Proton‐Promoted Nickel‐Catalyzed Asymmetric Hydrogenation of Aliphatic Ketoacids

et al. 2022

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A robust and highly active homogeneous chiral nickel–phosphine complex for the asymmetric hydrogenation of aliphatic γ‐ and δ‐ketoacids has been discovered. The hydrogenation could proceed smoothly in the presence of 0.0133 mol% catalyst loading (S/C=7500). The coordination chemistry and catalytic behavior of Ni(OTf)2 with (S,S)‐Ph‐BPE were explored by 1H NMR and HRMS. The mechanistic studies revealed that a proton promoted the activation of the substrate C=O bond and controlled the stereoselectivity through hydrogen bonds. A series of chiral γ‐ and δ‐alkyl substituted lactones were obtained in high yields with excellent enantioselectivities (up to 98 % yield and 99 % ee). In addition, this catalytic system also demonstrated that levulinic acid produced from a biomass feedstock was converted into chiral γ‐valerolactone without loss of ee value.

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Section: Resultsmentioning

confidence: 99%

Proton‐Promoted Nickel‐Catalyzed Asymmetric Hydrogenation of Aliphatic Ketoacids

et al. 2022

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“…The latter using Wittig reaction with (4-carboxybutyl) triphenyl phosphonium ylide 31 [81] yielded the Z-olefin with high yield and stereoselectivity (Z : E = 99 : 1). [82] The yield and Zselectivity were investigated using various organic bases (KHMDS, NaHMDS, LiHMDS, KHMDS and t-BuOK) and molar equivalents of ylide. However, all of these bases yielded nearly identical selectivity, KHMDS gave a higher yield once utilized in 4.0 equiv.…”

Section: Applications Of Wittig Reaction In Total Synthesis Of Macrolmentioning

confidence: 99%

Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides

et al. 2020

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The Wittig reaction involves the synthesis of an alkene via the conversion of an aldehyde or ketone with the already generated ylide from a phosphonium salt. Significantly, when this important name reaction is employed the desired alkenes are constructed via a predictable manner, thus resultant particularly are useful in the total synthesis of natural products and synthetic complex organic compounds with definite geometric isomers, exhibiting diverse biological potencies. In this review we try to highlight the applications of the Wittig reaction as an efficient and attractive strategy in the total synthesis of macrolides from 2008 to 2020.

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“… 37 Very recently, the synthesis of ( R )-(–)-phoracantholide I and ( S )-(+)-phoracantholide I, two pheromones found in frogs of the family of mantillidae, has been achieved from ( R )-(+)-γ-valerolactone in high yields ( Scheme 3 ). 38 Also chemical strategies have been developed for the preparation of enantiopure-GVL. For instance, levulinic acid could be converted with 82% enantioselectivity into ( S )-GVL in the presence of a SEGPHOS ligand-modified ruthenium catalyst.…”

Section: Biomass Derived Chemical Space For the Synthesis Of Bio-actimentioning

confidence: 99%

Expanding the biomass derived chemical space

2017

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Stereoselective synthesis of (R)-(−) and (S)-(+)-phoracantholide I from (R)-(+)-γ-valerolactone

Cited by 15 publications

References 35 publications

Proton‐Promoted Nickel‐Catalyzed Asymmetric Hydrogenation of Aliphatic Ketoacids

Proton‐Promoted Nickel‐Catalyzed Asymmetric Hydrogenation of Aliphatic Ketoacids

Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides

Expanding the biomass derived chemical space

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