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Synfacts 2009(2): 0129-0129  
DOI: 10.1055/s-0028-1087608
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of ()-Punctaporonin C

Contributor(s): Philip Kocienski, Indu Dager
M. Fleck, T. Bach*
Technische Universität München, Garching, Germany
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Publication History

Publication Date:
22 January 2009 (online)

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Significance

Punctaporonin C is a caryophyllene-related sesquiterpene. Its unusual oxatetracyclo[6.3.2.0]-tridecane skeleton makes it different from the other members of the family as well as difficult to access synthetically. A stereoselective intramolecular [2+2] photocycloaddition of tetronate E played a key role in this first total synthesis of ()-punctaporonin C.