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Synfacts 2008(8): 0785-0785  
DOI: 10.1055/s-2008-1078533
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Spinosyn A

Contributor(s): Philip Kocienski, Stewart Eccles
S. M. Winbush, D. J. Mergott, W. R. Roush*
Scripps Florida, Jupiter and University of Michigan, Ann Arbor, USA
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Publikationsdatum:
23. Juli 2008 (online)

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Significance

Spinosyn A is generated by the soil microbe Saccharopolyspora spinosa. It is an insecticide that degrades rapidly in the environment and has low toxicity to beneficial insects. This paper reports the synthesis of spinosyn A by an intramolecular Diels-Alder (IMDA) reaction and investigates the stereochemical control exerted by temporary pendant directing groups.