ISSN:
0947-3440
Schlagwort(e):
Thromboxane B2 key intermediate
;
Glyceraldehyde, (R)-isopropylidene
;
γ-Lactones
;
cis-Annulation
;
Felkin Anh addition of vinyl cuprate
;
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
A six-step synthesis of the bicyclic lactone pyranoside 1, which has served as a key intermediate in numerous syntheses of thromboxane B2, from (R)-2,3-isopropylideneglyceraldehyde is described. In contrast to the previous syntheses of 1 the lactone part is prepared first and acts as a template in the annulation of the hemiketal unit. Further aspects of interest are the Felkin-Anh-controlled addition of vinyl cuprates to the acrylic ester 16 and the considerable rate difference in the formation of the γ-lactones 13, 14, 19, and 21 from the corresponding hydroxy acids.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/jlac.199519950482
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