Synthesis and structural determination of the C33–C42 fragment of symbiodinolide
2008; Elsevier BV; Volume: 50; Issue: 8 Linguagem: Inglês
10.1016/j.tetlet.2008.11.056
ISSN1873-3581
AutoresHiroyoshi Takamura, Yuichiro Kadonaga, Yoshi Yamano, Chunguang Han, Yoko Aoyama, Isao Kadota, Daisuke Uemura,
Tópico(s)Microbial Natural Products and Biosynthesis
ResumoAbstract Symbiodinolide ( 1 ) is a polyol macrolide with a molecular weight of 2859 mu. As one of the degradation reactions, cross-metathesis of 2 , which is a methyl ester of 1 , with ethylene was performed to give the C33–C42 degraded fragment 4 . The absolute configuration of 4 was estimated to be (36 S ,40 S ) by Mosher method. Stereoselective synthesis of 4 was achieved in 14 steps from l -aspartic acid. Synthetic bis-( S )- and ( R )-MTPA esters exhibited the spectroscopic data identical with those of bis-( S )- and ( R )-MTPA esters derived from the degraded fragment 4 . Thus, the absolute stereochemistry of 4 was elucidated to be (36 S ,40 S ).
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