A Direct and Convergent Approach to Penams and Penems

Planchenault, Denis; Wisedale, Richard; Gallagher, Timothy; Hales, Neil J.

doi:10.1021/jo962367l

Cited by 24 publications

(11 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A concise and flexible route to bicyclic sulfur-based β -lactam was reported by Hales and co-workers in 1997 [44]. azomethine ylide strategy for assembling bicyclic β -lactams constitutes a simple, versatile, and above all, direct synthesis of penams and penems.…”

Section: Synthesis Of Penicillinsmentioning

confidence: 99%

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Feng¹,

Tang²,

Liang³

et al. 2016

CTMC

1,512

641

View full text Add to dashboard Cite

The impact of the development of sulfur therapeutics is instrumental to the evolution of the pharmaceutical industry. Sulfur-derived functional groups can be found in a broad range of pharmaceuticals and natural products. For centuries, sulfur continues to maintain its status as the dominating heteroatom integrated into a set of 362 sulfur-containing FDA approved drugs (besides oxygen or nitrogen) through the present. Sulfonamides, thioethers, sulfones and Penicillin are the most common scaffolds in sulfur containing drugs, which are well studied both on synthesis and application during the past decades. In this review, these four moieties in pharmaceuticals and recent advances in the synthesis of the corresponding core scaffolds are presented.

show abstract

Section: Synthesis Of Penicillinsmentioning

confidence: 99%

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Feng¹,

Tang²,

Liang³

et al. 2016

CTMC

1,512

641

View full text Add to dashboard Cite

show abstract

“…Recently, we disclosed a new and highly convergent cycloaddition strategy for the synthesis of bicyclic b-lactams 2, encompassing carbapenems and D 1 -carbapenems (Scheme 1), 1 as well as the sulfur-based penams and penems. 2 A critical step in this sequence involves the fragmentation of a b-lactam-based oxazolidinone 1 to release a reactive 1,3-dipole (a stabilised azomethine ylide); evidence for the structure of this key reaction intermediate is presented here.…”

mentioning

confidence: 96%

The azomethine ylide strategy for β-lactam synthesis: the structure of the key 1,3-dipolar intermediate

Wisedale¹,

Gallagher²,

Martel³

et al. 1997

Chem. Commun.

Self Cite

View full text Add to dashboard Cite

“…Azomethine ylides were also used in the synthesis of indolizines [26] and other natural products [12] [27 ± 29], recent examples being those of epibatidine and epiboxidine, which were found to have potential analgesic activity [30] [31]. On the other hand, analogous reactions with thiocarbonyl compounds leading to 1,3-thiazolidines are rarely described [32 ± 37], but recently, Gallagher and co-workers published an elegant synthesis of penam and penem skeletons by 1,3-dipolar cycloadditions of azomethine ylides with thioketones [38].…”

mentioning

confidence: 99%

Synthesis of an Enantiomerically Pure 1,3-Thiazole-5(4H)-thione and Its Stereoselective 1,3-Dipolar Cycloaddition with an Azomethine Ylide

Gebert¹,

Heimgartner²

2002

HCA

View full text Add to dashboard Cite

Starting from the enantiomerically pure 2H-azirin-3-amines (R,S)-4 and (S,S)-4, the enantiomeric, optically active 4-benzyl-4-methyl-2-phenyl-1,3-thiazole-5(4H)-thiones (R)-1 and (S)-1, respectively, have been prepared (Schemes 2 and 3). In each case, the reaction of 1 with N-(benzylidene)[(trimethylsilyl)methyl]amine (2) in HMPA in the presence of CsF and trimethylsilyl triflate gave a mixture of four optically active spirocyclic cycloadducts (Scheme 4). Separation by preparative HPLC yielded two pure diastereoisomers, e.g., (4R,5R,9S)-10 and (4R,5R,9R)-10. The regioisomeric compounds 11 were obtained as a mixture of diastereoisomers. The products were formed by a 1,3-dipolar cycloaddition of 1 with in situ generated azomethine ylide 3, which attacks 1 stereoselectively from the sterically less-hindered side, i.e., with (R)-1 the attack occurs from the reside and in the case of (S)-1 from the si-side.1. Introduction. ± Since the first [2 3] cycloadditions, described by Huisgen and coworkers [1 ± 5], azomethine ylides became a well-known class of 1,3-dipoles, and they found many applications in the synthesis of five-membered heterocycles [6 ± 17]. The 1,3-cycloaddition with olefins and acetylenes has frequently been used for the preparation of pyrrolidines and pyrroles with a large range of substitution [3] [7] [18 ± 24], and DeShong et al. described an intramolecular variation for the synthesis of bicyclic pyrrolidines and pyrroles [25]. Azomethine ylides were also used in the synthesis of indolizines [26] and other natural products [12] [27 ± 29], recent examples being those of epibatidine and epiboxidine, which were found to have potential analgesic activity [30] [31]. On the other hand, analogous reactions with thiocarbonyl compounds leading to 1,3-thiazolidines are rarely described [32 ± 37], but recently, Gallagher and co-workers published an elegant synthesis of penam and penem skeletons by 1,3-dipolar cycloadditions of azomethine ylides with thioketones [38]. Convenient methods to generate nonstabilized azomethine ylides are the desilylation of a-silyliminium salts [11] [12] [39] [40] and a-cyano-a'-silylamines, [32] or the treatment of a-silylated imines with trimethylsilyl triflate [41] (for other methods see [42 ± 50]).For many years, our research interest has been focused on the reactivity of the thiocarbonyl group in 1,3-dipolar cycloaddition reactions [51 ± 56]. In the last few years, we reported on the cycloadditions of azomethine ylides with aromatic thioketones [57] [58] and 1,3-thiazole-5(4H)-thiones [59] [60]. Recently, we reported on a stereoselective cycloaddition of an azomethine ylide, generated via thermal ring opening of cis-1-methyl-2,3-diphenylaziridine, with a chiral 1,3-thiazole-5(4H)-thione [61].

show abstract

A Direct and Convergent Approach to Penams and Penems

Cited by 24 publications

References 15 publications

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

The azomethine ylide strategy for β-lactam synthesis: the structure of the key 1,3-dipolar intermediate

Synthesis of an Enantiomerically Pure 1,3-Thiazole-5(4H)-thione and Its Stereoselective 1,3-Dipolar Cycloaddition with an Azomethine Ylide

Contact Info

Product

Resources

About