The cobalt way to vitamin B6

Parnell, Carol A.; Peter, K.; Vollhardt, C.

doi:10.1016/s0040-4020(01)91418-8

Cited by 75 publications

(15 citation statements)

References 40 publications

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“…158 In a very clever strategy, Vollhardt designed the synthesis to proceed through union of the symmetrical diyne 116 with acetonitrile ( 117 ). Due to the symmetry of 116 , there is no opportunity to deliver a regioisomer in the [2+2+2].…”

Section: Metallacycle-mediated Cross-coupling By [2+2+2]mentioning

confidence: 99%

Metallacycle-mediated cross-coupling in natural product synthesis

2016

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Section: Metallacycle-mediated Cross-coupling By [2+2+2]mentioning

confidence: 99%

Metallacycle-mediated cross-coupling in natural product synthesis

2016

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“…50 This methodology was applied in the total synthesis of vitamin B 6 . 51,52 In 1983, they succeeded in applying Z 5 -cyclopentadienyldicarbonylcobalt in the cyclization of 1,2-bis(propargyl)-1,2,3,4-tetrahydroisoquinolines with alkynes. 53 This procedure provides a novel synthetic entry into various tetrahydroprotoberberine nuclei.…”

Section: Six-membered and Other Heterocyclesmentioning

confidence: 99%

CHAPTER 5. Cobalt-Catalyzed Heterocycle Synthesis

2014

Catalysis Series

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Cobalt has the chemical configuration [Ar]4s 2 3d 7 and has oxidation states Co(II) and Co(III). Cobalt has many applications in a wide range of areas. In materials, cobalt is primarily used as the metal, for example, in the preparation of magnetic, wear-resistant and high-strength alloys. In biology, cobalt is the active center of coenzymes called cobalamins, the most common example of which is vitamin B 12 . As such, it is an essential trace dietary mineral for all animals. Cobalt in inorganic form is also an active nutrient for bacteria, algae and fungi. In chemistry, various cobalt compounds are used as oxidation catalysts in chemical reactions. Cobalt acetate is used for the conversion of xylene to terephthalic acid, the precursor to the bulk polymer poly(ethylene terephthalate). Typical catalysts are the cobalt carboxylates (known as cobalt soaps). They are also used in paints, varnishes and inks as 'drying agents' through the oxidation of drying oils. The same carboxylates are also used to improve the adhesion of steel to rubber in steel-belted radial tires. Cobalt-based catalysts are also important in reactions involving carbon monoxide. In this chapter, the applications of cobalt catalysts in the synthesis of heterocycles is discussed. Five-Membered HeterocyclesIn 1986, Pattenden and co-workers reported a cobalt-promoted oxidative freeradical cyclization of alkyl bromides, 1 by which functionalized butyrolactones were selectively formed in good yields. In 1990, a convenient method for the stereoselective preparation of trans-2-hydroxymethyltetrahydrofurans by the oxidative cyclization of 5-hydroxy-1-alkenes was developed by Inoki and Mukaiyama. 2 They used bis(1-morpholinocarbamoyl-4,4-dimethyl-1,3-pentanedionato)cobalt(II) [Co(modp) 2 ] as the catalyst with molecular oxygen as the RSC Catalysis Series No.

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“…The synthetic potential of the cobalt(I)-catalyzed cotrimerization of , -bis(trimethylstannyl)-diynes was demonstrated by the synthesis of vitamin B 6 ((106), Fig. (29)) [59]. Cyclization of the diyne (101) with acetonitrile gave bis(trimethylstannyl) furo [3,4-c]pyridine (102).…”

Section: Iv-4 [2+2+2] Cycloadditionsmentioning

confidence: 99%

Cycloadditions, Cycloisomerizations and Related Reactions of Alkynes Bearing Group 13 or 14 Heteroelements

Gandon¹,

Aubert²,

Malacrìa

2005

COC

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Cycloaddition and cycloisomerization reactions involving alkynes grant a rapid access to arenes, cyclic dienes, and cyclopentenone derivatives. The use of alkynes substituted by group 13 or 14 heteroelements as partners for such reactions is an emerging strategy. Indeed, the specific electronic properties of these heteroelements can play a crucial role for controlling the chemo-and regioselective outcome of a given reaction. Moreover, the heteroatoms can be considered as latent functional groups and would allow for further transformations including Suzuki-Miyaura or Stille crosscouplings. Both aspects will be presented in this review.

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The cobalt way to vitamin B6

Cited by 75 publications

References 40 publications

Metallacycle-mediated cross-coupling in natural product synthesis

Metallacycle-mediated cross-coupling in natural product synthesis

CHAPTER 5. Cobalt-Catalyzed Heterocycle Synthesis

Cycloadditions, Cycloisomerizations and Related Reactions of Alkynes Bearing Group 13 or 14 Heteroelements

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