Highly Efficient Synthesis of the Natural Spiro-Terpenoid (±)-Andirolactone

Orduña, Arturo; Zepeda, L. Gerardo; Tamariz, Joaquı́n

doi:10.1055/s-1993-25866

Cited by 41 publications

(17 citation statements)

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“…[19] Another synthesis of spiro-terpenoid (�)-andirolactone has been reported from the reaction of diacetyl and 4-nitrobenzoyl chloride in five steps (Scheme 2). [20] Norbert Krause reported a short stereoselective synthesis of racemic andirolactone in two steps (58% overall yield) by the reaction of 4-methylcyclohex-3-en-1-one with lithiated methylpropynoate and lithium diisopropylamide (LDA) followed by treatment with Gilman reagent (Scheme 3). [21] LambertellolsA and B (2), containing novel dihydronaphthalene-1(2H)-ones with spirobutenolide skeleton, have been isolated from Lambertella sp.1346.…”

Section: Natural Products and Biological Active Motifs With Spirobutementioning

confidence: 99%

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Yadav

Pratap

Ram³

2020

Asian J Org Chem

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Spirobutenolides and spirobutyrolactones structural motifs are widespread in various natural products that exhibit a broad array of biological activities. Additionally, their synthetic analogues also serve as biologically active compounds and building blocks of complex molecules. Owing to the wide range of pharmacological activities and structural diversity of the spirobutenolides and spirobutyrolactones, various efficient synthetic methodologies have been established to construct such interesting scaffolds. In the past decades, numerous total syntheses of spirobutenolides and spirobutyrolactones containing natural products have been reported. Structurally diverse spirobutenolides and spirobutyrolactones have been synthesized by using singlet oxygen, Mannich reaction, aldol condensation, rearrangement reaction , Reformatsky reaction, Michael-addition cyclization, Diels-Alder reaction, photocyclization reaction, and pericyclic reactions. Recently, metal-catalyzed cyclization, photocatalyzed radical cyclization, Baylis-Hillman reaction, asymmetric organocatalysis, NHC catalysis, ring contraction reactions, and hypervalent iodine catalysis have emerged as powerful tools to architect these nuclei. This review gives an overview of advancements in chemically and biologically relevant spirobutenolides and spirobutyrolactones of natural and synthetic origin. It also covers the newer methodologies for the construction of natural as well as synthetic spirobutenolides and spirobutyrolactones along with their potential applications.

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Section: Natural Products and Biological Active Motifs With Spirobutementioning

confidence: 99%

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Yadav

Pratap

Ram³

2020

Asian J Org Chem

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“…IR spectrum, ν, cm -1 : 3280 (NH), 2225 (CN), 1680 (C=O), 1635 (C=C), 1620 (C=C). 1 The IR spectra were recorded on a Specord 75IR spectrometer from samples dispersed in mineral oil. The 1 H NMR spectra were obtained on a Varian Mercury-300 spectrometer at 300 MHz using DMSO-d 6 -CCl 4 (1 : 3) as solvent and tetramethylsilane as internal reference.…”

Section: N-cyclohexyl-2-dicyanomethylidene-4-methyl-55-pentamethylenmentioning

confidence: 99%

Synthesis and some chemical transformations of N-cyclohexyl-2-imino-4-methyl-5,5-pentamethylene-2,5-dihydrofuran-3-carboxamide

Avetisyan¹,

Karapetyan²

2009

Russ J Org Chem

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“…In a pathway to racemic chrysolic acid, the deethoxycarbonylation of 29 with DMSO, NaCN and water (140)(141)(142)(143)(144)(145)(146)(147)(148)(149)(150) o C, 10 h) led to intermediate 30 (60%). The enantiomeric β-keto ester 35 on treatment with DMF, NaCl and water (reflux, 9 h) led to the de-t-butoxycarbonylated pyrrolidine 36-(3R) (92%).…”

Section: O Omentioning

confidence: 99%