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

The concise syntheses of (−)-habiterpenol and (+)-2,3- epi -habiterpenol from (3a R )-(+)-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...

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Veröffentlicht in:Organic & biomolecular chemistry 2023-08, Vol.21 (3), p.6129-6133
Hauptverfasser: Taguchi, Haruki, Kawaguchi, Mayuko, Nagamitsu, Tohru, Ohtawa, Masaki
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Zusammenfassung:The concise syntheses of (−)-habiterpenol and (+)-2,3- epi -habiterpenol from (3a R )-(+)-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. The concise synthesis of (−)-habiterpenol in 11 steps was enabled by MHAT-initiated redox radical cyclization of alkenylsilane.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01062g