Asymmetric synthesis of the constitutive C22-carboxylic acid of macroviracin A

Kanojia, Seema V.; Chatterjee, Sucheta; Gamre, Sunita; Chattopadhyay, Subrata; Sharma, Anubha

doi:10.1016/j.tet.2015.01.010

Cited by 7 publications

(2 citation statements)

References 34 publications

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“…The synthetically valuable unsaturated ketones could be obtained from alcohols in a one-pot protocol including sequential alkylation and deacetylation , (Scheme ). The enantiomeric purity of the deacetylation products was well preserved from the alkylation products ( 5a – 5e ).…”

Section: Results and Discussionmentioning

confidence: 99%

Regio- and Enantioselective Rhodium-Catalyzed Allylic Alkylation of Racemic Allylic Alcohols with 1,3-Diketones

Tang

Zhang

et al. 2018

J. Am. Chem. Soc.

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Highly regio- and enantioselective rhodium-catalyzed allylic alkylation of 1,3-diketones with racemic secondary allylic alcohols is reported. In the presence of a Rh-catalyst derived from the Carreira (P, olefin)-ligand and TFA as an additive, chiral branched α-allylated 1,3-diketones could be obtained in good to excellent yields, with excellent regio- and enantioselectivity ( b/ l > 19/1, 86-98% ee). The direct utilization of allyl alcohols as electrophiles represents an improvement from the viewpoint of an atom economy. Both aryl- and aliphatic-substituted allyl alcohols are suitable substrates with excellent reaction outcomes. This reaction features mild conditions, broad substrate scope, and readily available substrates.

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Section: Results and Discussionmentioning

confidence: 99%

Regio- and Enantioselective Rhodium-Catalyzed Allylic Alkylation of Racemic Allylic Alcohols with 1,3-Diketones

Tang

Zhang

et al. 2018

J. Am. Chem. Soc.

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“…In this regard biocatalytic reactions offer green and sustainable alternative routes to develop asymmetric syntheses of pharmaceuticals with varied stereochemical features [30–33]. Our group has been using lipases for the chemoenzymatic syntheses of several bioactive molecules [34–39]. The prevalence of PhCH(OH) in 2 , and in many other biochemicals, attracted our attention to formulate an enantioselective lipase-catalyzed transacetylation strategy to obtain a suitable molecule bearing the designated chiral segment (compound 2 , vide infra).…”

Section: Introductionmentioning

confidence: 99%

A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12

Kanojia

Chatterjee

Chattopadhyay

et al. 2019

Beilstein J. Org. Chem.

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A chemoenzymatic synthesis of the title compound has been developed using an efficient and highly enantioselective lipase-catalyzed acylation in a hydrophobic ionic liquid, [bmim][PF6], followed by a diastereoselective asymmetric dihydroxylation as the key steps for incorporating the stereogenic centers. The further conversion to the appropriate intermediates and subsequent acylation with lauric acid furnished the target compound.

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First Total Synthesis of the Proposed Structure of Pandangolide 1

2018

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The first total synthesis of the proposed structure of pandangolide 1 is reported. The synthesis was carried out using both an organocatalytic approach and a chiral‐pool approach. The required stereochemistry at C‐3 and C‐5 was installed by using an organocatalytic aldol reaction and a stereoselective ketone reduction. The construction of the 12‐membered core was achieved by 2‐methyl‐6‐nitrobenzoic anhydride‐mediated Shiina lactonization. The structure of target molecule was confirmed unambiguously by single‐crystal X‐ray analysis, but the optical rotation and NMR spectroscopic data of the synthetic pandangolide 1 were found to be inconsistent with the natural product.

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Asymmetric synthesis of the constitutive C22-carboxylic acid of macroviracin A

Cited by 7 publications

References 34 publications

Regio- and Enantioselective Rhodium-Catalyzed Allylic Alkylation of Racemic Allylic Alcohols with 1,3-Diketones

Regio- and Enantioselective Rhodium-Catalyzed Allylic Alkylation of Racemic Allylic Alcohols with 1,3-Diketones

A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12

First Total Synthesis of the Proposed Structure of Pandangolide 1

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