Synthesis of allenyl prostaglandins

Crabbé, Pierre; Carpio, Humberto

doi:10.1039/c39720000904

Cited by 27 publications

(12 citation statements)

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“…In the first synthesis of this isomeric mixture (Scheme 38), [119] the allenic moiety was installed by an S N 2'-reduction of the propargylic acetate 110 with lithium dimethylcuprate. [115,120] Subsequent manipulation of the protective groups and oxidation of the 9-OH group finally provided the target molecule 107. During the last decade, a substantial number of novel (sometimes even stereoselective) strategies for the preparation of allenic prostaglandins have been devised.…”

Section: Prostaglandins and Carbacyclinsmentioning

confidence: 99%

Synthesis and Properties of Allenic Natural Products and Pharmaceuticals

2004

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Nowadays, about 150 natural products comprising an allenic or cumulenic structure are known. The chemistry of these compounds has turned out to be a very attractive and prolific area of interest: advances in the isolation and characterization of new allenic natural products have led to the establishment of efficient synthetic procedures which in many cases also open up an access to enantiomerically pure target molecules. Inspired by the intriguing biological activities of many allenic natural products, allene moieties are now systematically introduced in pharmacologically active classes of compounds (steroids, prostaglandins, amino acids, nucleosides). The functionalized allenes thus obtained often exhibit impressive activities as mechanism-based enzyme inhibitors, cytotoxic, or antiviral agents. A prerequisite for further developments in this field is the efficient stereoselective synthesis of allene derivatives.

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Section: Prostaglandins and Carbacyclinsmentioning

confidence: 99%

Synthesis and Properties of Allenic Natural Products and Pharmaceuticals

2004

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“…Compound 1 has the greater luteolytic effect. [1][2][3] Crabbe and Carpio, [2] for example, added the acetate of 4-pentyne-1-ol to Corey's lactol [2,[4][5][6][7][8] and generated the propadiene unit from the resulting propargylic acetate using lithium dimethyl cuprate. [1][2][3] Crabbe and Carpio, [2] for example, added the acetate of 4-pentyne-1-ol to Corey's lactol [2,[4][5][6][7][8] and generated the propadiene unit from the resulting propargylic acetate using lithium dimethyl cuprate.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of (E,Z)-5-Bromo-1,1-dimethoxy-5-trimethylsilyl-4-pentene, an Upper Chain Allenic Prostaglandin Building Block

2003

Synthetic Comm.

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This work explores the synthetic route to allenic prostaglandins. In a search for more efficient and reliable methods for the introduction of the allene moiety into the side chains of prostaglandins, the synthons, the (E ) and (Z) isomers of 1-bromo-5,5-dimethoxy-1-trimethylsilyl-1-pentene (13a) and (13b), have been prepared and converted to R,S-1,1-dimethoxy-6-phenyl-4,5-hexadiene (16), a prostaglandin analog.

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“…*Author to whom correspondence should be addressed. A We have also used the "classical" Skattebel approach [5] to build the pregnane and corticoid chains. Indeed, a significant step in the total synthesis of steroids is the elaboration of the pregnane and tri-oxygenated corticoid chains at position 17 [8].…”

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confidence: 99%

“…Indeed, a significant step in the total synthesis of steroids is the elaboration of the pregnane and tri-oxygenated corticoid chains at position 17 [8]. The allenyl steroid (7) was obtained by addition of dibromocarbene to the 17-methylene steroid (5), thus giving the dibrornocyclopropyl derivative (6). Fragmentation of the gem-dibromo-adduct (6) with methyllithium afforded the prepadiene steroid (7) in about 56% yield.…”

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confidence: 99%

“…The acid halide (3c) was then readily converted into the corresponding allenic acid (3d) [4J. It was further demonstrated that treatment of the acid fluoride (3c) with dimethylcadmium provided a mixture of allenyl methylketones (3e) and (3f), thus constituting an easy entry to allenyl ketones [5], not readily available by other methods. A number of unusual trisubstituted allenyl steroids were obtained by this approach and submitted to biological screening [6] .…”

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confidence: 99%

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