Synthesis of ent-nanolobatolide

Angewandte Chemie - International Edition

Volumn 50, Issue 18, 2011, Pages 4165-4168

  Cheng, Hau Man ^a   Tian, Weiwei ^a   Peixoto, Philippe A ^a   Dhudshia, Bhartesh ^a   Chen, David Y K ^a  

^a INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

Author keywords

biomimetic synthesis; cyclization; cycloaddition; natural products; neurological agents

Indexed keywords

BIOMIMETIC SYNTHESIS; BIOSYNTHETIC PATHWAY; INTERMOLECULAR DIELS-ALDER REACTIONS; MENTHONE; NATURAL PRODUCTS; NAZAROV CYCLIZATION; NEUROLOGICAL AGENTS; NEUROPROTECTIVE AGENTS; OPENING REACTIONS; RING EXPANSION; TOTAL SYNTHESIS;

BIOMIMETICS; CYCLOADDITION; SYNTHESIS (CHEMICAL);

CYCLIZATION;

BRIDGED COMPOUND; NANOLOBATOLIDE; NEUROPROTECTIVE AGENT;

ARTICLE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

BRIDGED COMPOUNDS; CYCLIZATION; NEUROPROTECTIVE AGENTS; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 79955419320     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201100926     Document Type: Article

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29. Notably, although (+)-menthone, which would lead to the naturally occurring form of (+)-nanolobatolide (1) in accordance to our synthetic strategy, is less readily available and more expensive than (-)-menthone, both enantiomeric forms of menthol are readily available, and this compound can be easily oxidized to give (+) and (-)-menthone.