Enantioselective total synthesis of (+)-neosymbioimine.
[reaction: see text] The enantioselective total synthesis of (+)-neosymbioimine was accomplished in 18 steps from (-)-(S)-citronellol utilizing an organocatalytic alpha-oxidation of aldehyde 6. The carbon core was constructed by a tandem Horner-Wadsworth-Emmons (HWE) reaction and an intramolecular Diels-Alder cyclization. All double bonds of 12 were made in a stereoselective manner by Wittig-type reactions. Selective formation of the monosulfate monoester was accomplished by one-pot excessive sulfation followed by kinetic hydrolysis of bissulfate 18 in 79% yield.
Varseev
Georgy N
GN
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany.
Maier
Martin E
ME
D000080462:Acyclic Monoterpenes; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D006868:Hydrolysis; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry; D013237:Stereoisomerism
D000080462:Acyclic Monoterpenes; D006575:Heterocyclic Compounds, 3-Ring; D039821:Monoterpenes; C505669:neosymbioimine; C007078:citronellol