A practical synthesis of (E)-2-cyclopentadecen-1-one: an important precursor of macrocyclic muscone

Tetrahedron Letters

Volumn 49, Issue 3, 2008, Pages 548-551

  Hisanaga, Yusuke ^a   Asumi, Yuya ^a   Takahashi, Masaki ^a   Shimizu, Yasuhiro ^a   Mase, Nobuyuki ^a   Yoda, Hidemi ^a   Takabe, Kunihiko ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

Author keywords

Elimination; Macrocycles; Muscone

Indexed keywords

2 CYCLOPENTADECEN 1 ONE; 2 MESYLOXYCYCLOPENTADECANONE; MACROCYCLIC COMPOUND; MAGNESIUM DERIVATIVE; METHYLMAGNESIUM CUPRATE; MUSCONE; SEBACIC ACID; SULFURIC ACID; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; OLEFINATION; PRECURSOR; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 37449028765     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.065     Document Type: Article

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38. We also prepared some other macrocyclic enones by the use of the same synthetic procedure (Table 3, entry 5); (E)-cycloicos-2-enone (y. 98%), (E)-cyclohexadec-2-enone (y. 98%), (E)-cyclotridec-2-enone (y. 66%), and (E)-cyclododec-2-enone (y. 38%). Elimination reactions of less than 10-membered ring mesylates did not proceed, probably due to a highly labile cyclopropyl cationic intermediate.
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