Access to C-15 macrocyclic ketones by iterative fragmentations of a tricyclic system

Angewandte Chemie - International Edition

Volumn 41, Issue 23, 2002, Pages 4523-4526

  Fehr, Charles ^a   Galindo, José ^a   Etter, Olivier ^a   Thommen, Walter ^a  

^a Email:   (Switzerland)

Author keywords

Fragmentation; Fragrances; Ketones; Macrocycles; Reduction

Indexed keywords

ITERATIVE METHODS; KETONES; SYNTHESIS (CHEMICAL);

TRICYCLIC SYSTEM;

STEREOCHEMISTRY;

CARBON; DIHYDROXYKETONE; KETONE DERIVATIVE; MACROCYCLIC COMPOUND; MUSK; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; FRAGMENTATION REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037011313     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021202)41:23<4523::AID-ANIE4523>3.0.CO;2-1     Document Type: Article

References (21)

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16. The factors that govern "internal" versus "external" hydride attacks are not yet fully understood.
17. Here, Red-Al® reduction at room temperature led to a 43:57 diastereomeric mixture of alcohol 8 and its diastereomer (85%). At -70°C no reduction was observed.
18. This reaction was not tested with larger amounts of reagent.
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