Highly Diastereoselective Synthesis of Manoyl Oxide Derivatives by TiCl4-Catalyzed Nucleophilic Cleavage of Ambracetal Derivatives

Synlett

Volumn , Issue 15, 2003, Pages 2313-2316

  Barrero, A F ^a   Alvarez Manzaneda Roldan E J ^a   Romera Santiago, J L ^a   Chahboun, R ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

Acetal cleavage; Labdane diterpenes; Lewis acids; Manoyl oxides; Natural products

Indexed keywords

19 HYDROXYMANOYL OXIDE; 2 CYANOOXANE; ACETAL DERIVATIVE; AMBRACETAL DERIVATIVE; DITERPENE; LEWIS ACID; MANOYL OXIDE DERIVATIVE; NITRILE; OXEPANE DERIVATIVE; POTASSIUM CYANIDE; TITANIUM TETRACHLORIDE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYST; DIASTEREOISOMER; DRUG SYNTHESIS; REACTION TIME; STEREOCHEMISTRY; TEMPERATURE;

EID: 0347380059     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42124     Document Type: Article

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45. 4 and evaporated to give a crude product which was chromatographed (hexane-t-BuOMe, 3:2) to yield 14 and 15.
46. 3), 146.7 (C-14), 111.4 (C-15), 77.1 (C-8), 74.4 (C-13), 63.2 (C-17), 56.9* (C-9), 51.4* (C-5), 51.3 (19-COOMe), 43.8 (C-4), 40.0 (C-1), 38.1 (C-3), 37.8 (C-10), 37.7 (C-6), 33.0 (C-12), 30.0 (C-14), 28.6 (C-18), 21. 5 (C-7), 19.1 (C-2), 15.1 (C-11), 13.0 (C-20).