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Synthesis of (4E,7S)-(−)-7-Methoxy-4-tetradecenoic Acid, a Major Constituent of the Marine CyanophyteLyngbya Majuscula

✍ Scribed by Müller, Claudia ;Voss, Gundula ;Gerlach, Hans

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
428 KB
Volume
1995
Category
Article
ISSN
0947-3440

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✦ Synopsis

The metabolite of the marine cyanophyte Lyngbya majuscula yield the alkyne 2 which could easily be transformed into the (4E,?S)-(-)-?-methoxy-4-tetradecenoic acid (1) has been target molecule. Hydrogenation with Lindlar catalyst produsynthesized for the first time in optically active form in eight ced 7 which could be isomenzed to 8 with ( E ) configuration. steps in 20% overall yield. Heptyloxirane (3) and the alkyne Methylation of the 7-hydroxy group in 8 gave 9 which could 4 containing the carboxyl group masked as a tricyclic orthobe transformed into the methyl ester 10 and the (4E,?S)-acid ester were prepared by known methods from 5 and 6 as star-1 in high yield. ting materials. Reaction of lithiated 4 with 3 afforded in 74%

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