21499-64-9Relevant articles and documents
The synthesis of d6-α-Farnesene
Fielder,Rowan
, p. 1075 - 1085 (1994)
d6-α-Farnesene (3,7-dimethyl-11-2H3-methyl-12,12,12-2H3-dodeca-1,3E,6E,10 -tetraene) has been synthesised by two routes. Thermolysis of 2-geranyl-3-methylsulpholene (5) yielded unlabelled α-famesene (93%) which was epoxidized at Δ10 in 31% yield. Oxidative cleavage of the epoxide (42%) and Wittig elaboration of the resultant trienal with d6-isopropyl triphenylphosphorane gave d6-α-farnesene (73%). Alternatively, selective epoxidation of (5) gave the terminal 6',7' mono-epoxide in 74% yield. Oxidative cleavage (73%) and Wittig elaboration of the resultant aldehyde yielded deuterated 2-geranyl-3-methylsulpholene (46%). Thermal elimination of sulphur dioxide afforded the title compound in 91% yield.
Anti-Carbometalation of Homopropargyl Alcohols and Their Higher Homologues via Non-Chelation-Controlled Syn-Carbometalation and Chelation-Controlled Isomerization
Ma, Shengming,Negishi, Ei-Ichi
, p. 784 - 785 (1997)
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Enantioselective Conversion of Oligoprenol Derivatives to Macrocycles in the Germacrene, Cembrene, and 18-Membered Cyclic Sesterterpene Series
Reddy, D. Srinivas,Corey
supporting information, p. 16909 - 16913 (2018/12/14)
A new enantio-and diastereoselective process has been developed for the efficient conversion of farnesol and other oligoprenyl alcohols to chiral 10-, 14-, and 18-membered cyclization products, including germacrenol, (+)-costunolide, 3-β-elemol, and epi-mukulol. The key cyclization reaction utilizes ω-bromo aldehyde substrates, a chiral ligand, and indium powder as the reagent at -78 °C and generates 10-, 14-, and 18-membered cyclic products in 70-74% yield and 94-95% ee.
A general and efficient method for the palladium-catalysed conversion of allylic alcohols into their corresponding dienes
Ostrowski, Karoline A.,Vogelsang, Dennis,Vorholt, Andreas J.
, p. 1302 - 1305 (2016/03/09)
A general method was established, converting a broad range of allylic alcohols directly and quantitatively into their corresponding dienes. The developed protocol allows the direct use of allylic alcohols, circumventing the need for their derivatisation into more reactive precursors, thereby minimising waste production with water as the sole co-product.