An Efficient Asymmetric Synthesis of Prostaglandin E1

Rodrı́guez, Ana R.; Nomen, Miguel; Spur, Bernd W.; Godfroid, Jean‐Jacques

doi:10.1002/(sici)1099-0690(199910)1999:10<2655::aid-ejoc2655>3.0.co;2-2

Cited by 44 publications

(9 citation statements)

References 47 publications

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“…Aiming at the crucial cycloaldolization, we had to unmask an aldehyde functionality at the C-7 terminus; to do this, we decided to exploit a slightly modified version of the Swern oxidation, [12] which, fortunately enough, could be directly applied to a protected primary hydroxy group. Thus, 8 was first subjected to complete protection of its free OH groups as triethylsilyl ethers to give lactone 9 (TESOTf, pyridine, DMAP, 95%), which underwent direct oxidation to aldehyde 10 [DMSO, (COCl 2 ) 2 ; then Et 3 N, 98%].…”

Section: Synthesis Of 5a-carba-β-d-gulopyranose (1) and 5a-carba-β-d-mentioning

confidence: 99%

Synthesis of a Small Repertoire of Non-Racemic 5a-Carbahexopyranoses and 1-Thio-5a-carbahexopyranoses

et al. 2002

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A short and practical entry to optically pure 5a-carbahexopyranose and 1-thio-5a-carbahexopyranose representatives is described. Besides a few functional group and protecting group manipulations, the synthetic scheme counts on two fundamental carbon−carbon bond-forming reactions, namely (i) a regio-and stereoselective aldol addition between heterocyclic (silyloxy)diene donors (6 or 13) and D-glyceral-

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Section: Synthesis Of 5a-carba-β-d-gulopyranose (1) and 5a-carba-β-d-mentioning

confidence: 99%

Synthesis of a Small Repertoire of Non-Racemic 5a-Carbahexopyranoses and 1-Thio-5a-carbahexopyranoses

et al. 2002

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“…Several representatives of this group of compounds have been successfully resolved using various lipases and acylating reagents. [4][5][6][7][8][9] However, to the best of our knowledge no reports on the preparation of closely related optically active 4-hydroxy-5alkylcyclopent-2-en-1-ones (2, Fig. 1), are available in the literature.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Approach to Optically Active 4‐Hydroxy‐5‐alkylcyclopent‐2‐en‐1‐one Derivatives: An Application of a Combined Circular Dichroism Spectroscopy and DFT Calculations to Assignment of Absolute Configuration

et al. 2014

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A series of representative optically active derivatives of 4-hydroxy-5-alkylcyclopent-2-en-1-one were prepared from the respective 2-furyl methyl carbinols via the Piancatelli rearrangement followed by the enzymatic kinetic resolution of racemates. Applicability of chiroptical methods (experimental and calculated electronic circular dichroism [ECD] and vibrational circular dichroism [VCD] spectra) to determine the absolute configuration of both stereogenic centers in 4-hydroxy-5-methylcyclopent-2-en-1-one was demonstrated. It was also demonstrated that the concurrent application of ECD and VCD spectroscopy can be used for the determination of the configuration of two stereogenic centers.

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“…The primary silyl ether was then oxidised selectively under Swern conditions to afford the aldehyde 14. [10] This two-step sequence allowed the facile differentiation of the primary and secondary hydroxyl groups. Scheme A Wittig olefination of aldehyde 14 resulted in the formation of the terminal alkene 15, which was envisaged to be a good starting material for the introduction of the cyclopropane carboxylic acid moiety.…”

Section: Resultsmentioning

confidence: 99%