Synthesis of Enantiomerically Pure β-Lactones by the Tandem Aldol−Lactonization. A Highly Efficient Access to (3S,4S)-3-Hexyl-4- [(2S)-2-hydroxytridecyl]oxetan-2-one, the Key Intermediate for the Enzyme Inhibitors Tetrahydrolipstatin and Tetrahydroesterastin,1

Wedler, C.; Costisella, Burckhard; Schick, H.

doi:10.1021/jo980292a

Cited by 29 publications

(9 citation statements)

References 26 publications

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“…[249] In the following years, a number of structurally closely related lipase inhibitors were discovered, like valilactone, panclicin D and others. [250,251] Esterastin was already known since 1978 (Fig. 5.109).…”

Section: Regulation Of Fat Resorptionmentioning

confidence: 97%

“…It is a solid, which may be purified by crystallisation. [250] This was the main reason for Hoffmann-La Roche to develop the saturated compound rather than the natural product as a drug for adiposity (Fig. 5.112).…”

Section: Syntheses Of Tetrahydrolipstatinmentioning

confidence: 98%

“…[250] The protected hydroxy-aldehyde is reacted with the amide enolate from 1-octanoylbenzotriazole and lithium hexamethyldisilazide. The preferential formation of the anti-aldol product can be explained by the Zimmerman-Traxler model.…”

Section: Industrial Synthesis Of Witegamentioning

confidence: 99%

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Pharmaceuticals

Schaefer

2014

Natural Products in the Chemical Industry

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A boy who is born in Germany today has a probable life expectancy of around 77 years, and a girl one of 82 years -twice as long as in the year 1880. This increase is a consequence of both, better living circumstances -working conditions, food, clothing, housing -, and also a result of more comprehensive medical care. Thus, a whole range of infectious diseases has been wiped out, or brought at least under control, and the mortality rate for civilisation-and age-related diseases has dropped. Vaccinations and drugs play a key role in this outcome. The 20th century is characterised especially by the worldwide blossoming of the pharmaceutical industry. More and more, the targeted search for and development of new drugs have replaced serendipitous discoveries (Fig. 5.1). Pharmaceuticals of the last century.

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Section: Regulation Of Fat Resorptionmentioning

confidence: 97%

Section: Syntheses Of Tetrahydrolipstatinmentioning

confidence: 98%

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Pharmaceuticals

Schaefer

2014

Natural Products in the Chemical Industry

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“…Shick et al disclosed an efficient three-step procedure for the synthesis of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one 50a, which is a common intermediate for the preparation of 45. This procedure featured a one-pot tandem aldol lactonization of lithium enolate 49 with aldehyde 48 (Scheme 11) [28].…”

Section: Four-membered Ringsmentioning

confidence: 99%

Benzotriazole-Mediated Synthesis of Oxygen-Containing Heterocycles

Bol’shakov

2015

Topics in Heterocyclic Chemistry

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This review aims at delivering an overview of the synthetic utility of benzotriazole and its derivatives for the preparation of oxygen-containing heterocycles. This review serves both as a synthetic guide and as a theoretical handbook of benzotriazole-assisted preparations of oxygen heterocycles and offers a complete overview of existing applications for benzotriazole and its derivatives in heterocyclic synthesis. Multiple examples reveal the superiority of benzotriazole-based approaches over conventional ones.

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“…[3,4] There has been considerable interest in tetrahydrolipstatin due to the growing awareness of obesity-related illness and several syntheses have been reported. [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] In each case the construction of the strained trans-β-lactone of (1) emerges as an important synthetic challenge. The majority of previously reported syntheses [5][6][7][8][9][10][11][12][13][14][15][16] use Adams' conditions for formation of the β-lactone from a β-hydroxy carboxylic acid precursor.…”

Section: Introductionmentioning

confidence: 99%