Novel oxidative conversion of β,γ-unsaturated acids into butenolides: synthesis of heritonin and heritol

Zubaidha, P. K.; Govande, Chitra A.; Rao, Y. T. S.

doi:10.1039/c39940001101

Cited by 16 publications

(4 citation statements)

References 12 publications

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“…This strategy has been used by Chavan and co-workers for conversion of β , γ-unsaturated acids into butenolides mediated by CAN. They applied this protocol for the synthesis of biologically active molecules such as heritonin …”

Section: 2 Alkoxylation Reactionsmentioning

confidence: 99%

Cerium(IV) Ammonium NitrateA Versatile Single-Electron Oxidant

2007

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He was a visiting scientist at Columbia University during 1979−82 and Visiting professor at the University of Pernambuco in Brazil in May 2001. He is a fellow of the Indian Academy of Sciences and a Silver Medalist of the Chemical Research Society of India. His research interests include cycloadditions, radical-mediated C−C and C−heteroatom bond-forming reactions, multicomponent reactions, and heterocyclic synthesis. Forty students have completed Ph.D. degrees under his supervision, and he has published nearly 200 papers in major international journals. Ani Deepthi was born in Kollam, Kerala State, India, in 1980. She obtained her B.Sc. degree from Kerala University (Fatima Mata National College, Kollam) in 2000 and her M.Sc. degree (First Rank) from the Cochin University of Science and Technology in 2002. She did her doctoral research under the guidance of Dr. Vijay Nair in the Regional Research Laboratory (CSIR) Trivandrum, working in the area of multicomponent reactions and has submitted her Ph.D. thesis to the

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Section: 2 Alkoxylation Reactionsmentioning

confidence: 99%

Cerium(IV) Ammonium NitrateA Versatile Single-Electron Oxidant

2007

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“…79 Later on, another group in the same institute reported that b,g-unsaturated esters can be converted into butenolides in high yield by oxidative cyclization with ceric ammonium nitrate (CAN) at room temperature. 80 The above-reported approaches to butenolides both started from a-tetralone, and differed only in how the butenolide ring was constructed. In 2004, Silveria reported a new strategy to (AE)-heritonin, which employed b-tetralone as the starting compound (Scheme 3).…”

Section: Heritiera Littoralismentioning

confidence: 99%

Natural products from semi-mangrove flora: source, chemistry and bioactivities

Xiao

Pan

et al. 2009

Nat. Prod. Rep.

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This review covers the source, chemistry and bioactivities of natural products from semi-mangrove species worldwide. The chemotaxonomy of semi-mangrove plants and total synthesis of heritol analogues, which are potential biocompatible pesticides, are discussed.1 Introduction, 2 Acanthaceae, 2.1 Acanthus, 2.1.1 Aliphatic glycosides, 2.1.2 Alkaloids, 2.1.3 Flavonoids, 2.1.4 Lignan glycosides, 2.1.5 Megastigmane and phenolic glycosides, 2.1.6 Phenylethanol glycosides, 2.1.7 Triterpenoids, 2.1.8 Miscellaneous, 2.1.9 Bioactivities, 3 Euphorbiaceae, 3.1 Excoecaria, 3.1.1 Diterpenoids, 3.1.2 Miscellaneous, 3.1.3 Bioactivities, 4 Lythraceae, 4.1 Pemphis acidula, 5 Sterculiaceae, 5.1 Heritiera littoralis, 5.1.1 Flavones, 5.1.2 Triterpenoids, 5.1.3 Benzene derivatives, 5.1.4 Sesquiterpenes, 5.1.5 Steroids, 6 Total syntheses of heritol and its analogues, 7 Chemotaxonomy and concluding remarks, 8 Acknowledgements 9 References.

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“…In continuation of our work in the synthesis of biologically active molecules viz. heritol 1, 2 heritonin 2, 3 heritianin 3, vallapin 4, 3 vallapianin 5 3 and related compounds we have reported 4,5 novel methodologies for the synthesis of butenolides from the corresponding b,g-unsaturated esters and acids.…”

mentioning

confidence: 96%

Novel oxidative conversion of β,γ-unsaturated acids into butenolides: synthesis of heritonin and heritol

Abstract: A novel strategy of converting P,y-unsaturated esters to butenolides involving oxidative cyclisation with ceric ammonium nitrate at room temperature is described.

Cited by 16 publications

References 12 publications

Cerium(IV) Ammonium NitrateA Versatile Single-Electron Oxidant

Cerium(IV) Ammonium NitrateA Versatile Single-Electron Oxidant

Natural products from semi-mangrove flora: source, chemistry and bioactivities

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

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