A new 2-azatricyclo[4.4.0.02,8]decenone synthesis and ketene formation by retro-Diels-Alder reaction

Schultz, Arthur G.; Dittami, James P.; Myong, Sun Ok; Sha, Chin Kang

doi:10.1021/ja00348a051

Cited by 49 publications

(17 citation statements)

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“…The resulting pale yellow solution was then stirred at 0 °C for fifteen minutes, tri- n -butyltin hydride (1 equiv) was added dropwise, and the reaction mixture left to stir for a further 15 min. The resulting n -Bu 3 SnLi [13] solution was cooled to −20 °C and CuBr·Me 2 S (0.5 equiv) added in one portion. The brown reaction mixture was left to stir for 30 min and subsequently cooled to −78 °C.…”

Section: Methodsmentioning

confidence: 99%

Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines

Jarvis¹,

McLaren²,

Osborn³

et al. 2013

Beilstein J. Org. Chem.

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Section: Methodsmentioning

confidence: 99%

Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines

Jarvis¹,

McLaren²,

Osborn³

et al. 2013

Beilstein J. Org. Chem.

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“…The first lengthy synthesis 106,107 rests upon the tetrathiafulvalene (TTF) induced so-called "radical-polar crossover" cascade [108][109][110] , which was used to construct the carbazolone (ABC) synthon. The Mitsunobu reaction with N-(2-nitrophenyl)methanesulfonamide initiated the transformation of 2-allylcyclohexenol to sulfonamide 302, which was then converted to diazonium salt 110 303.…”

Section: Carbazolones As Intermediatesmentioning

confidence: 99%

A Review on Recent Developments in Syntheses of the Post-Secodine Indole Alkaloids. Part I: The Primary Alkaloid Types

Hájíček¹

2004

Collect. Czech. Chem. Commun.

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This first part of a planned review on developments in the field of total and formal total synthesis of the post-secodine indole alkaloids concentrates on primary alkaloid types. It reviews the synthesis of secodine, aspidospermane, pseudoaspidospermane and ibogane alkaloids; andranginine is also included. It covers the literature from 1992-1993 up to approximately May 2004. A review with 179 references.

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“…The resulting pale yellow solution was then stirred at 0 °C for fifteen minutes, tri-nbutyltin hydride (1 equiv) was added dropwise, and the reaction mixture left to stir for a further 15 min. The resulting n-Bu 3 SnLi [13] solution was cooled to −20 °C and CuBr·Me 2 S (0.5 equiv) added in one portion. The brown reaction mixture was left to stir for 30 min and subsequently cooled to −78 °C.…”

Section: Ring-opening Reaction With Methyl Magnesium Grignardmentioning

confidence: 99%

“…These strained bifunctional heterocycles possess considerable synthetic flexibility and undergo a range of efficient transformations [1][2][3][4][5][6][7][8][9]. Whilst there has been a recent resurgence in the development of reactions using vinyl aziridines, there have been few contemporary reports of new methods for their synthesis [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29]. However, a key limitation to the synthetic application of aziridines in general is the nature of the N-substituent: most synthetic routes to aziridines deliver N-sulfonylated products, and the cleavage of the sulfonamide bond is often challenging.…”

Section: Introductionmentioning

confidence: 99%