Biosynthetic studies of marine lipids. 11. Synthesis, biosynthesis, and absolute configuration of the internally branched demospongic acid, 22-methyl-5, 9- …

D Raederstorff, AYL Shu, JE Thompson…

Index: Raederstorff, Daniel; Shu, Arthur Y.L.; Thompson, Janice E.; Djerassi, Carl Journal of Organic Chemistry, 1987 , vol. 52, # 12 p. 2337 - 2346

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Citation Number: 79

Abstract

The 14C-labeled short-chain fatty acid 10-methylhexadecanoic acid (10-Me-160) as well as its hitherto undescribed 10R and 10s antipodes was incorporated into the marine sponge Aplysina fistularis and transformed in situ into 22-methyl-5, 9-octacosadienoic acid (22-Me- A5s9-28: 2) by chain elongation. No qualitative specificity between the two enantiomers was observed.[3H] Methionine was also incorporated into the sponge to investigate the ...