ISSN:
0170-2041
Keywords:
Corey lactone
;
Prostaglandins
;
Free radical cyclization
;
Glyceraldehyde, (R)-isopropylidene
;
Radicals
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Asymmetric eight-step syntheses are reported for the ent-Corey lactone alcohol derivatives 3a-d and their epimers 4a-d and 14a, b from (R)-2,3-isopropylidene glyceraldehyde (5) as the starting material. The key step of the synthesis is the free radical cyclization of the butenolide thiocarbonates 11, 12 and 13. This reaction produces 3 and 4 in ratios between 57:43 and 30:70 from 11 and 12, whereas 14a and 14b are generated from 13 in a ratio of 19:81. From 3d the prostanoid enone 18 is prepared via the configurationally stable aldehyde 17.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199419940602
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