Divergent Cycloaddition and Ring-Closing Metathesis Approaches to Indolizidine and Pyrrolo[1,2-<i>a</i>]azepine Skeletons from a Chiral Precursor:  An Expeditious Route to (−)-8-<i>epi</i>-Swainsonine Triacetate

Nath, Madhumita; Mukhopadhyay, Ranjan; Bhattacharjya, Anup

doi:10.1021/ol052716a

Cited by 29 publications

(2 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Analogues of swainsonine synthesised during the period under review include (−)-8-epi-swainsonine 32 10 and its triacetate, 11 both by routes involving ring-closing metathesis. New sulfonium ion analogues of swainsonine include the triols (−)-33 12 and (−)-34.…”

Section: Swainsonine and Related Compoundsmentioning

confidence: 99%

Indolizidine and quinolizidine alkaloids

2008

View full text Add to dashboard Cite

This review covers the isolation, structure determination, synthesis, chemical transformations and biological activity of indolizidine and quinolizidine alkaloids. Included in the review are the hydroxylated indolizidines lentiginosine, swainsonine, castanospermine and their analogues; alkaloids from animal sources, including arthropods and amphibians; alkaloids from the genera Polygonatum, Prosopis and Poranthera; phenanthroindolizidine and phenanthroquinolizidine alkaloids; Nuphar alkaloids; lupine alkaloids; and alkaloids from marine sources. 130 references are cited.

show abstract

Section: Swainsonine and Related Compoundsmentioning

confidence: 99%

Indolizidine and quinolizidine alkaloids

2008

View full text Add to dashboard Cite

show abstract

“…The second generation Grubbs catalyst 3 was found to promote better results than 2. [44][45][46] The nature of the hydroxy protecting groups plays also an important role in the outcome of the reaction probably by decreasing pyrrolidine ring flexibility (isopropylidene group) or by increasing steric hindrance (TBS group). RCM of 2-allyl-N-alkenylpiperidines 36 and 38 afforded the quinolizidine skeleton of two natural products, epiquinamide and mitralactonine, in good yields (Scheme 13 and Scheme 14).…”

Section: A-substituted Azacyclesmentioning

confidence: 99%

Olefin Metathesis of Amine‐Containing Systems: Beyond the Current Consensus

Compain¹

2007

Adv Synth Catal

164

View full text Add to dashboard Cite

Olefin metathesis is one of the most powerful synthetic tool to access amine-containing heterocycles and alkaloids. A major drawback associated with the use of amines concerns their ability to coordinate to metal-alkylidene complexes and to interfere unproductively with catalytic activity. Based on literature precedents, it has been established as a "dogma" that efficient metathesis reactions are suppressed in the presence of basic amines and that such substrates must invariably be deactivated by conversion of the amines to the corresponding carbamates or ammonium salts. However, an increasing number of examples of amine-containing compounds that are good substrates for metathesis is being reported in the literature. How can this "non-classical" reactivity be rationalized and exploited? The purpose of this review is to provide an overview of successful metathesis reactions performed with aminecontaining compounds in order to allow some guidelines to be formulated. A special emphasis is placed on the different parameters that may influence the outcome of the reaction such as steric effects, amine basicity, and the nature of the catalyst.

show abstract

Olefin Ring‐Closing Metathesis

Yet

2016

Organic Reactions

View full text Add to dashboard Cite

The olefin ring‐closing metathesis reaction catalyzed by ruthenium and molybdenum complexes has been employed in the syntheses of carbocycles, heterocycles, supramolecular compounds, and in tandem metathesis reactions. Chiral ruthenium and molybdenum catalysts have provided high enantiomeric and diastereomeric excesses in ring‐closing metathesis reactions. Many of the unsuccessful medium‐ and large‐sized ring formations which were unsuccessful by traditional methods, such as the intramolecular Wittig, Horner–Wadsworth–Emmons, and Julia–Kocienski reactions, can now be formed by olefin ring‐closing metathesis reactions. Ring‐closing metathesis has been a key step and sometimes the only successful method for the synthesis of numerous natural products and drug discovery targets. The objective of this chapter is to provide an updated, comprehensive coverage of the literature of the olefin ring‐closing metathesis reaction and related processes. Key mechanistic points are summarized.

show abstract

Divergent Cycloaddition and Ring-Closing Metathesis Approaches to Indolizidine and Pyrrolo[1,2-a]azepine Skeletons from a Chiral Precursor: An Expeditious Route to (−)-8-epi-Swainsonine Triacetate

Cited by 29 publications

References 31 publications

Indolizidine and quinolizidine alkaloids

Indolizidine and quinolizidine alkaloids

Olefin Metathesis of Amine‐Containing Systems: Beyond the Current Consensus

Olefin Ring‐Closing Metathesis

Contact Info

Product

Resources

About