Attempted Syntheses of Pelletierine

King, John A.; Hofmann, Vera; McMillan, Freeman H.

doi:10.1021/jo50001a012

Cited by 28 publications

(6 citation statements)

References 36 publications

(44 reference statements)

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“…Finally, removal of the Cbz group by hydrogenation provided pelletierine (58) in high yield. Although its structure is relatively simple compared to other complex members of this family, 24 this compound has been the target for numerous synthetic groups. 25 Scheme 8 Total synthesis of pelletierine…”

Section: Scheme 7 Intramolecular Heteroatom Michael Reactionmentioning

confidence: 99%

Lycopodium Alkaloids: An Intramolecular Michael Reaction Approach

Saha¹,

Carter²

2017

Synlett

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The Lycopodium alkaloids possess a rich history that has captured the attention of synthetic chemists across the globe. This large family consists of over 250 known natural products with diverse structural features and noteworthy biological activity. Herein, we interweave the synthetic accomplishments by others in the field with our own unified strategy to accessing multiple subfamilies of the Lycopodium alkaloids. This discussion includes lycopodine, the C10-hydroxy Lycopodium alkaloids (10-hydroxylycopodine, deacetylpaniculine and paniculine), pelletierine, cermizine D, fastigiatine, himeradine A, clavolonine and 7-hydroxylycopodine. A unifying feature of much of the work discussed within this account is the use of intramolecular Michael additions to construct key ring systems within the Lycopodium alkaloids. Examples include the use of an intramolecular keto-sulfone Michael reaction and an intramolecular heteroatom Michael reaction.1 General Background on Lycopodium Alkaloids2 Development of a Strategy for Lycopodium Alkaloids2.1 Generalized Strategy2.2 Known Syntheses of C10-Functionalized Lycopodium Alkaloids3 Quinolizidine-Type Alkaloids3.1 Background3.2 Development of the Heteroatom Michael Reaction3.3 Synthesis of the Core Lycopodine Building Block: Pelletierine3.4 Total Synthesis of Cermizine D3.5 Synthesis of the Eastern Half of Himeradine A4 Lycopodine-Type Alkaloids4.1 Total Syntheses of Lycopodine4.1.1 Earlier Racemic Syntheses4.1.2 Approach Toward the Tricyclic Skeleton of Lycopodine: Intramolecular Mannich4.1.3 Enantioselective Total Syntheses of Lycopodine4.2 Total Syntheses of Clavolonine (8-Hydroxylycopodine)4.3 Total Synthesis of 7-Hydroxylycopodine4.4 Synthetic Route for 10-Hydroxy Lycopodium Alkaloids4.4.1 Background4.4.2 Total Syntheses4.4.3 Impact of the C10-Stereochemistry5 Conclusion

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Section: Scheme 7 Intramolecular Heteroatom Michael Reactionmentioning

confidence: 99%

Lycopodium Alkaloids: An Intramolecular Michael Reaction Approach

Saha¹,

Carter²

2017

Synlett

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“…By F. M. Miller Received June 3,1953 Previous attempts at preparation of the highly unstable pomegranate alkaloid pelletierine (I) have been made by hydrolysis of its acetal,1•2 available from the corresponding pyridine compound by hydrogenation, and by lithium aluminum hydride reduction of 3-ketoóctahydropyrrocoline.3 These methods failed, presumably due to aldolization catalyzed by the basic piperidine nitrogen atom.…”

Section: Reduction Of 3-(2-pyridyl)-propionaldehydementioning

confidence: 99%

The Indicator and Dye Properties of Some Aromatic Phosphonic Acids and their Arsenic Analogs

Kosolapoff¹,

Priest²

1953

J. Am. Chem. Soc.

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“…11 Pelletierine (2.1) was first isolated from pomegrante by Tanret in 1878. Despite its deceptively simple structure, 12 this compound has been the target of considerable synthetic attention and numerous total syntheses. 13,14 Many of the quinolizidine-natural products identified by Ayer, Kobayashi and others are derived from pelletierine through the pelletierine condensation.…”

Section: Introduction To Quinolizidine Containing Alkaloidsmentioning

confidence: 99%