Concise syntheses of (-)-habiterpenol and (+)-2,3- epi -habiterpenol via redox radical cyclization of alkenylsilane

Concise syntheses of (-)-habiterpenol and (+)-2,3- epi -habiterpenol via redox radical cyclization of alkenylsilane

The concise syntheses of (-)-habiterpenol and (+)-2,3- -habiterpenol from (3a )-(+)-sclareolide and 6-methoxyindanone in 11 and 12 steps, respectively, were enabled by the regioselective addition of the TMS-indenyl anion and the facile stereoselective metal hydride hydrogen atom transfer (MHAT)-init...

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Veröffentlicht in:Organic & biomolecular chemistry 2023-08, Vol.21 (30), p.6129-6133
Hauptverfasser: Taguchi, Haruki, Kawaguchi, Mayuko, Nagamitsu, Tohru, Ohtawa, Masaki
Format: Artikel
Sprache:eng
Schlagworte:
Hydrogen atoms
Metal hydrides
Stereoselectivity
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Zusammenfassung:The concise syntheses of (-)-habiterpenol and (+)-2,3- -habiterpenol from (3a )-(+)-sclareolide and 6-methoxyindanone in 11 and 12 steps, respectively, were enabled by the regioselective addition of the TMS-indenyl anion and the facile stereoselective metal hydride hydrogen atom transfer (MHAT)-initiated redox radical cyclization of alkenylsilane.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01062g