A convenient synthesis of trans-sabinene hydrate from (−)-3-thujol via a highly selective ene reaction of singlet oxygen

A convenient synthesis of trans-sabinene hydrate from (−)-3-thujol via a highly selective ene reaction of singlet oxygen

trans-Sabinene hydrate ( 1), was synthesized from (−)-3-thujol ( 2) in four steps. The key step was the selective formation of trans-2-hydroxy-3-thujene ( 6) by photooxygenation of a 3:1 mixture of 2- and 3-thujenes ( 4 and 5) obtained from (−)-3-thujol mesylate ( 3). Hydrogenation of 6 gave compoun...

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Veröffentlicht in:Bioorganic & medicinal chemistry 1996-03, Vol.4 (3), p.419-421
Hauptverfasser: Baeckström, Peter, Koutek, Bohumir, Šaman, David, Vrkoč, Jan
Format: Artikel
Sprache:eng
Schlagworte:
Animals
Bridged Bicyclo Compounds - chemistry
Chromatography, Thin Layer
Coleoptera - chemistry
Magnetic Resonance Spectroscopy
Monoterpenes
Oxygen - chemistry
Pheromones - chemical synthesis
Stereoisomerism
Terpenes - chemical synthesis
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Zusammenfassung:trans-Sabinene hydrate ( 1), was synthesized from (−)-3-thujol ( 2) in four steps. The key step was the selective formation of trans-2-hydroxy-3-thujene ( 6) by photooxygenation of a 3:1 mixture of 2- and 3-thujenes ( 4 and 5) obtained from (−)-3-thujol mesylate ( 3). Hydrogenation of 6 gave compound 1 in 46% overall yield. Graphic
ISSN:0968-0896
1464-3391
DOI:10.1016/0968-0896(96)00020-X