Synthesis of seven-membered oxacycles. Part 2: The furan approach

Fall, Yagamare; Vidal, Beatriz; Alonso, David Martín; Gómez, Generosa

doi:10.1016/s0040-4039(03)01027-x

Cited by 40 publications

(13 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The obtained butenolide 36 is a key intermediate in the synthesis of polycyclic ethers such as 37 [51]. The obtained butenolide 36 is a key intermediate in the synthesis of polycyclic ethers such as 37 [51].…”

Section: Furan As C-4 Synthon 31 Synthesis Of 14-dicarbonyl Compoundsmentioning

confidence: 98%

Furan Oxidations in Organic Synthesis: Recent Advances and Applications

Merino¹,

Tejero²,

Delso³

et al. 2007

COC

View full text Add to dashboard Cite

show abstract

Section: Furan As C-4 Synthon 31 Synthesis Of 14-dicarbonyl Compoundsmentioning

confidence: 98%

Furan Oxidations in Organic Synthesis: Recent Advances and Applications

Merino¹,

Tejero²,

Delso³

et al. 2007

COC

View full text Add to dashboard Cite

show abstract

“…Finally, the ring junction was determined by NMR experiments and established as transbicyclic lactone 48, containing an oxepane ring. [23,24]…”

Section: Eurjocmentioning

confidence: 99%

“…Adapted from refs. [23,24] are far less represented in the synthesis of seven-membered cyclic ethers.…”

Section: Oxidative-reductive Cyclizationsmentioning

confidence: 99%

Synthesis of Seven Membered Oxacycles: Recent Developments and New Approaches

et al. 2020

View full text Add to dashboard Cite

This minireview focuses on recent advances in the synthesis of seven-membered ring oxacycles, whether saturated, unsaturated, fused or isolated. We cover a remarkable variety of strategies and methods developed during the past two decades, based mainly on cyclizations, ring-closing metathesis, conjugate additions, and ring expansions. The cyclizations can be generated directly or triggered through an oxocarbenium ion, carbocation or iminium-type species. Also discussed [a] Prof.

show abstract

“…Our research group developed some years ago a new and original methodology for the synthesis of oxacyclic systems based on the oxidation of a furan ring with singlet oxygen, which we coined "the furan approach 6 . We anticipated that IL-supported furan 2, could undergo a singlet oxygen oxidation to afford methoxy butenolide 12, which after protecting group removal would give bicyclic lactone 13, via an oxa Michael addition (Scheme 3).…”

Section: Scheme 2 Synthesis Of Il Supported Furanmentioning

confidence: 99%

“…Electrospray mass spectra (ESI-MS) were measured on a Bruker APEXQe FT-ICR MS 2-azidoethyl 4-methylbenzenesulfonate (9). To a solution of NaN3 5.8 g (89.6 mmol, 2equiv) in water (70 mL) was added a portionwise 3.00 mL (44.8 mmol, 1equiv) of 3-chloroethanol (6). The mixture was heated under reflux for 16 h, then cooled to room temperature and extracted with CH2Cl2 (60 mL x 3).…”

Section: General Proceduresmentioning

confidence: 99%