Asymmetric Total Synthesis of (−)‐Maoecrystal V
CHEMISTRY-AN ASIAN JOURNAL(2015)
Abstract
The asymmetric total synthesis of (-)-maoecrystalV, a novel cytotoxic pentacyclic ent-kaurane diterpene, has been accomplished. Key steps of the current strategy involve an early-stage semipinacol rearrangement reaction for the construction of the C10 quaternary stereocenter, a rhodium-catalyzed intramolecular O-H insertion reaction, and a sequential Wessely oxidative dearomatization/intramolecular Diels-Alder reaction to forge the pentacyclic framework of maoecrystalV.
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Key words
asymmetric synthesis,diels-alder reaction,rhodium,semi-pinacol rearrangement,total synthesis
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