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ChemInform Abstract: Stereoselective Synthesis of the Pheromone (R)-(-)-Sulcatol, and Its Enantiopure (R)- and (S)-1-Mono, -1,1-Di-, and -1,1,1-Trifluoro Analogues.

โœ Scribed by Alberto Arnone; Pierfrancesco Bravo; Walter Panzeri; Fiorenza Viani; Matteo Zanda

Publisher
John Wiley and Sons
Year
2010
Weight
39 KB
Volume
30
Category
Article
ISSN
0931-7597

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โœฆ Synopsis

Sulcatol (VIII) and three of its enantiomeric fluoro analogues (XI) are prepared in five steps and with good overall yields, starting from nearly equimolar mixtures of C-3 epimers of sulfoxides (I), (IX), (X), and the known trifluoro derivative. Reduction of the sulfoxides to the corresponding ฮฒ-hydroxy derivatives is the key step in the synthetic sequence, best accomplished under chelation control conditions using iBu 2 AlH/ZnBr 2 . With the diastereomeric mixtures of the resulting alcohols in hand, the preparation of both enantiomers of sulcatol analogues (XI) via the route demonstrated for alcohol (+)-(II) is possible. -(ARNONE, ALBERTO; BRAVO, PIERFRANCESCO; PANZ-

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Stereoselective Synthesis of the Pheromo
Stereoselective Synthesis of the Pheromone (R)-(โ€“)-Sulcatol, and Its Enantiopure (R)- and (S)-1-Mono-, -1,1-Di-, and -1,1,1-Trifluoro Analogues[1]
โœ Alberto Arnone; Pierfrancesco Bravo; Walter Panzeri; Fiorenza Viani; Matteo Zand ๐Ÿ“‚ Article ๐Ÿ“… 1999 ๐Ÿ› John Wiley and Sons ๐ŸŒ English โš– 285 KB ๐Ÿ‘ 1 views

The pheromone (R)-(-)-sulcatol (10a) and three of its starting from chiral (R)-2-methyl-5-[(4-methylphenyl)sulfinyl]pent-2-ene (1) and commercially available fluorinated enantiomeric mono-, di-, and trifluoro analogues 10b-d have been synthesized, in six steps and with good overall yields, or non-fl