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Synfacts 2007(1): 0010-0010  
DOI: 10.1055/s-2006-955652
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Jimenezin

Contributor(s): Philip Kocienski
N. G. Bandur, D. Brückner, R. W. Hoffmann*, U. Koert*
Philipps-Universität Marburg, Germany
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Publikationsdatum:
15. Dezember 2006 (online)

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Significance

Jimenezin is one of the few annonaceous acetogenins to harbour a tetrahydropyran ring. The principal challenge in the synthesis is the construction of fragment F in which three of the stereogenic centers were created using substrate-controlled reactions starting with the single stereogenic center in lactol A. The sequence of reactions leading from B to F is noteworthy.