ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The Li/K-derivative 6 is used to synthesize the title compounds (3a and 4a) in enantiomerically pure form from (-)-(S)-propylene epoxide. The C,C bond forming key step leading to the hydroxyketone 7 is followed by cyclization (→, 8), Beckmann cleavage (→ 9b) and hydrolysis to 3a (recently isolated from civet). Base treatment of 3a opens the ring (10) to give the hydroxyacid 1 which is cyclized to the macrolide 4a. The synthetic usefulness of the highly nucleophilic doubly reduced dienone system 6 as d5-reagent (see synthons 2) is thus demonstirated.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19790620322