Eu(fod)3-catalyzed rearrangement of allylic esters possessing a chelating site. Application to enediyne synthesis

Tetrahedron Letters

Volumn 40, Issue 12, 1999, Pages 2397-2400

  Dai, Wei Min ^a   Lee, Mavis Yuk Ha ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYLDIALKYNE DERIVATIVE; ALLYL COMPOUND; ANTINEOPLASTIC ANTIBIOTIC; ESTER; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; CHELATION; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TEMPERATURE;

EID: 0033583188     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00276-2     Document Type: Article

References (17)

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15. 13C NMR, IR, and MS.
16. 2Ph were synthesized from phthalic dicarboxaldehyde in 8 steps (see ref. 3b).
17. 8. Chiral ester 1h (92% ee; t = 21.5′ over Chiralcel OD column, hexane-i-PrOH = 97:3, 1 mL/min, UV 254 nm; for the other enantiomer, t = 20.2′) was prepared from the (-)-allyl alcohol. The latter was synthesized through asymmetric reduction of the ketone using (+)-DIP-Chloride. HPLC profile of chiral enediyne 2h: 84% ee; t = 31.5′ over Chiralcel OD column, hexane-i-PrOH = 97:3, 1 mL/min, UV 254 nm; for the other enantiomer, t = 33.3′. The absolute stereochemistry of chiral 1h and 2h is not determined.