1,2,2-tribromocyclopropanecarboxylic acid and derivatives—Valuable intermediates for four carbon cyclopropane and cyclopropene synthons

Dulayymi, Ahmad R. Al; Dulayymi, Juma’a R. Al; Baird, Mark S.; Gerrard, Michelle E.; Koza, Gani; Harkins, S. D.; Roberts, Evan

doi:10.1016/0040-4020(95)01123-4

Cited by 24 publications

(16 citation statements)

References 32 publications

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“…This convergent total synthesis of neofinaconitine (47) by Shi, Tan, and co-workers in 2013 was designed to begin with an intermolecular Diels-Alder cycloaddition between the in situ generated diene from enone 69 and cyclopropene 70 (Scheme 2). 27 To allow for this strategy, the cyclopentenone intermediate 69 was prepared from commercially available furfuryl alcohol, 58 while the cyclo- (-)-isoatisine (29) lepenine (58) cochlearenine (59) dihydroajaconine (60) 53,54 N-ethyl-1-hydroxy-17-veratroyldictyzine (61) gymnandine (62) paniculamine (63) (±)-spiramine C (64) (±)-spiramine D (65) azitine (66) cossonidine (67) septedine (68) C. Dank et al…”

Section: Total Synthesis Of Neofinaconitinementioning

confidence: 99%

“…propene starting material 70 was prepared in 6 steps from methyl acrylate. 59 Notably, due to the rapid Alder-ene dimerization of the cyclopropene intermediate, this compound was isolated and was used immediately in the cycloaddition reaction. The Diels-Alder cycloaddition was conducted by addition of intermediate 70 directly to the in situ prepared diene from intermediate 69.…”

Section: Syn Thesismentioning

confidence: 99%

“…In a unifying approach to the C 18 -, C 19 -, and C 20 -diterpenoid alkaloids, the Sarpong group accomplished the preparations of weisaconitine D (48), liljestrandinine (52), as well as the denudatine-type compounds cochlearenine (59), N-ethyl-1-17-veratroyldictyzine (61), and paniculamine (63). 4a The advanced intermediate 93 is common to all of these natural product syntheses.…”

Section: Total Synthesis Of Liljestrandininementioning

confidence: 99%

“…The Sarpong group embarked on the mammoth task to design a route that was suitably amenable to modifications at the latest possible stage and yet still access 59, 63, and 61/241; three denudatine-type diterpenoid alkaloids (Scheme 16). 52 This was achieved by designing a route to intermediate cochlearenine (59); from 59, following a few late-stage manipulations of the functional groups on the bicyclo[2.2.2] structural element, each of the intended targets was successfully accessed. Starting from 93, which the Sarpong group had previously designed and accessed in 10 steps (25% overall yield), 28 the primary alcohol was converted into the corresponding aldehyde 230 via a Swern oxidation.…”

Section: Total Syntheses Of Cochlearenine N-ethyl-1hydroxy-17-veratmentioning

confidence: 99%

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Recent Advances Towards Syntheses of Diterpenoid Alkaloids

Dank¹,

Sanichar²,

Choo³

et al. 2019

Synthesis

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The diterpenoid alkaloids serve as a rich source of synthetic targets for organic chemists, due to the intriguing structure of the overlapping ring systems, along with biological activities commonly associated with compounds of this group. Fifteen total syntheses and numerous synthetic studies towards construction of ring fragments have been reported since 2010. This review article gives a brief overview of diterpenoid alkaloids and summarizes the recent synthetic efforts.1 Introduction1.1 Structural Classification and Biosynthetic Origin1.2 Structure Elucidation of the Aconitum Alkaloids2 Total Syntheses2.1 C18-Diterpenoid Alkaloids2.2 C19-Diterpenoid Alkaloids2.3 C20-Diterpenoid Alkaloids3 Strategies To Synthesize Ring Systems3.1 Radical-Based Cyclizations3.2 Ruthenium-Mediated Enyne Cycloisomerization3.3 Reductive Coupling3.4 Diels–Alder Reactions3.5 Oxidative Dearomatization/Diels–Alder Sequence3.6 Transannular Aziridation3.7 Intramolecular [5+2] Cycloaddition3.8 Miscellaneous4 Conclusion

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Section: Total Synthesis Of Neofinaconitinementioning

confidence: 99%

Section: Syn Thesismentioning

confidence: 99%

Section: Total Synthesis Of Liljestrandininementioning

confidence: 99%

Section: Total Syntheses Of Cochlearenine N-ethyl-1hydroxy-17-veratmentioning

confidence: 99%

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Recent Advances Towards Syntheses of Diterpenoid Alkaloids

Dank¹,

Sanichar²,

Choo³

et al. 2019

Synthesis

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“…[19] Dry hydrogen bromide gas (9.115 g, 112.6 mmol, 1.1 equiv.) was bubbled into tetraethylammonium bromide (2.582 g, 122.9 mmol, 1.2 equiv.)…”

Section: -Bromo-1-[(tert-butyldimethylsilyl)oxy]prop-2-ene (7)mentioning

confidence: 99%

Stereocontrol of the Intramolecular Diels−Alder Reaction by Internal Hydrogen Bonding

2003

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A novel approach for exo/endo stereocontrol of intramolecular Diels−Alder reactions is described. Substrates carrying a hydroxymethyl group attached to the diene and an ester group attached to the dienophile participate in hydrogen bonding in the transition state. This non-covalent interaction causes either a significant enhancement or diminution in the observed kinetic endo/exo product ratio. Thus, the parent pentadienyl maleate 12 undergoes intramolecular Diels−Alder reaction to give an approx. 5:1 mixture of transand cis-fused bicyclic cycloadducts, whereas the C2-hydro-

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Direct Construction of the 9H‐Pyrrolo[1,2‐a]azepin‐9‐amine Skeleton via [4+3] Annulation of Alkyl 2‐Aroyl‐1‐chlorocyclo‐ propanecarboxylates

Yang

Gong

2015

Adv Synth Catal

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Ad irect diastereoselective synthesis approach of important 9H-pyrrolo[1,2-a]azepin-9amines wase stablished via base-promoted [4+ +3] annulation between donor-acceptor reagents derived from 1H-pyrrole-2-carbaldehydesa nd alkyl 2-aroyl-1-chlorocyclopropanecarboxylates.T his transition metal-free domino reactionp roceeded quickly under mild basic conditions,a ffording potentially bioactive azepine derivatives in moderate to high yields with high diastereoselectivities (up to > 20:1). COMMUNICATIONSScheme3.Synthesis of azepino[1,2-a]indole.Scheme 4. Apossible mechanisticprocess for the [4+ +3] annulation reaction.

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1,2,2-tribromocyclopropanecarboxylic acid and derivatives—Valuable intermediates for four carbon cyclopropane and cyclopropene synthons

Cited by 24 publications

References 32 publications

Recent Advances Towards Syntheses of Diterpenoid Alkaloids

Recent Advances Towards Syntheses of Diterpenoid Alkaloids

Stereocontrol of the Intramolecular Diels−Alder Reaction by Internal Hydrogen Bonding

Direct Construction of the 9H‐Pyrrolo[1,2‐a]azepin‐9‐amine Skeleton via [4+3] Annulation of Alkyl 2‐Aroyl‐1‐chlorocyclo‐ propanecarboxylates

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