Asymmetric synthesis of (+)-loline

“…[187,189,199,[202][203][204][205][206][207][208][209] The synthesis of a particularly interesting member of the pyrrolidizine class of alkaloids, (+)-loline (202) was achieved by using an intramolecular acylnitroso HDA strategy (Scheme 37). [210,211] Hydroxamic acid 199 was oxidized to yield the oxazine 200. Subsequent modifications yielded the intermediate 201 which was converted into (+)-loline 202.…”

Section: Indolidizine and Pyrrolidizine Alkaloidsmentioning

confidence: 99%

The Nitrosocarbonyl Hetero‐Diels–Alder Reaction as a Useful Tool for Organic Syntheses

Bodnar¹,

2011

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Organic transformations that result in the formation of multiple covalent bonds within the same reaction are some of the most powerful tools in synthetic organic chemistry. Nitrosocarbonyl hetero-Diels–Alder (HDA) reactions allow for the simultaneous stereospecific introduction of carbon–nitrogen and carbon–oxygen bonds in one synthetic step, and provide direct access to 3,6-dihydro-1,2-oxazines. This Review describes the development of the nitrosocarbonyl HDA reaction and the utility of the resulting oxazine ring in the synthesis of a variety of important, biologically active molecules.

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“…8. The positive ECD band shifts from y203 nm at pH 2.49 in 6 to y200 nm in its disodium salt (148). Similarly, the positive ECD band shifts from y208 nm at pH 2.6 in 7 to y202 nm in its disodium salt (153) in water.…”

Section: Chiroptical Propertiesmentioning

confidence: 92%

Enantiomerically pure compounds related to chiral hydroxy acids derived from renewable resources

et al. 2012

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An inventory of enantiomerically pure compounds of agrochemical, pharmaceutical and of functional interest derived from naturally occurring chiral a-hydroxy acids has been presented. Attention has been focused on the employment of relatively less documented hydroxycitric acids namely isocitric, garcinia and hibiscus acids. Synthetic applications have been reviewed. The chiroptical studies on these new classes of compounds have also been presented.

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Asymmetric synthesis of (+)-loline

Cited by 28 publications

References 12 publications

Loline alkaloids: Currencies of mutualism

Loline alkaloids: Currencies of mutualism

The Nitrosocarbonyl Hetero‐Diels–Alder Reaction as a Useful Tool for Organic Syntheses

Enantiomerically pure compounds related to chiral hydroxy acids derived from renewable resources

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