High‐Pressure Selectivity Studies—A Simple Route to a Homochiral Wistarin Precursor

Knappwost-Gieseke, Costanze; Nerenz, F.; Wartchow, Rudolf; Winterfeldt, Ekkehard

doi:10.1002/chem.200204524

Cited by 18 publications

(8 citation statements)

References 73 publications

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“…[141] The newly formed spirobutenolides Cfurther underwent Diels-Alder reaction with cyclopentadiene and 1-methoxy-buta-1,3-diene separately to form endo adducts D and E respectively (Scheme 100). [142]…”

Section: Diels-alder Reactionmentioning

confidence: 99%

“…Spirobutenolide Spirobutenolide on reaction with nucleophiles such carbanion and alkoxy ion form Michael adducts (Scheme 108). [142]…”

Section: Oxidationmentioning

confidence: 99%

“…The diepoxide H was also obtained directly in one step by epoxidation with t-BuOOH for 15 h (Scheme 101). [142] The conjugated double bond of spirobutenolide I smoothly underwent dihydroxylation in the presence of RuCl 3 and sodium periodate to form J(Scheme 102). [87c]…”

Section: By Michael Addition Of 2-mercaptoacetaldehyde To 3-alkylidenmentioning

confidence: 99%

“…The reduction of spirobutenolides with different reducing agents preferentially reduces the double bond of the furan ring forming lactone (Scheme 103). [142] The use of different oxidizing agents reduced the conjugated bond of the furan ring (Scheme 104 and 105). [87c,d,23] Furans with a hydroxyalkyl group at the position-2 was anticipated to furnish spirocyclicbutenolides viaa double cyclization sequence (Scheme 106).…”

Section: By Michael Addition Of 2-mercaptoacetaldehyde To 3-alkylidenmentioning

confidence: 99%

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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: Diels-alder Reactionmentioning

confidence: 99%

“…Spirobutenolide Spirobutenolide on reaction with nucleophiles such carbanion and alkoxy ion form Michael adducts (Scheme 108). [142]…”

Section: Oxidationmentioning

confidence: 99%

Section: By Michael Addition Of 2-mercaptoacetaldehyde To 3-alkylidenmentioning

confidence: 99%

Section: By Michael Addition Of 2-mercaptoacetaldehyde To 3-alkylidenmentioning

confidence: 99%

See 2 more Smart Citations

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Yadav

Pratap

Ram³

2020

Asian J Org Chem

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show abstract

“…Lactones and butenolides are frequently found as substructures in the framework of natural products and employed in reaction published by Winterfeldt (Scheme 49) [74]. Lactones and butenolides are frequently found as substructures in the framework of natural products and employed in reaction published by Winterfeldt (Scheme 49) [74].…”

Section: Diels-alder Cycloadditions Of Heterocyles As Dienophile Compmentioning

confidence: 99%