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1983•Journal of the Chemical Society Chemical CommunicationsRequires access

Biosynthesis of cantharidin: evidence for the specific incorporation of C-4 and C-11? of farnesol

Wolf‐Dietrich Woggon, Suzanne Hauffe, Hans Schmid

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Abstract

(E,E)-[11′,12-3H2,2,4-14C]farnesol is specifically incorporated into cantharidin as shown by use of a new degradation involving a Diels–Alder/retro-Diels–Alder sequence; the incorporation of (E,E)-[11′-3H, 14C,2-14C]-farnesol (14) into cantharidin proceeds with 47%3H-retention whereby the 11′-14C label is randomised at C-9 and C-11 in cantharidin and the ratio [2-14C]/[11′-14C] of (14) is retained indicating an intramolecular conversion of farnesol into cantharidin.

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What this paper is about

(E,E)-[11′,12-3H2,2,4-14C]farnesol is specifically incorporated into cantharidin as shown by use of a new degradation involving a Diels–Alder/retro-Diels–Alder sequence; the incorporation of (E,E)-[11′-3H, 14C,2-14C]-farnesol (14) into cantharidin proceeds with 47%3H-retention whereby the 11′-14C label is randomised at C-9 and C-11 in cantharidin and the ratio [2-14C]/[11′-14C] of (14) is retained indicating an intramolecular conversion of farnesol into cantharidin.

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Available abstract

(E,E)-[11′,12-3H2,2,4-14C]farnesol is specifically incorporated into cantharidin as shown by use of a new degradation involving a Diels–Alder/retro-Diels–Alder sequence; the incorporation of (E,E)-[11′-3H, 14C,2-14C]-farnesol (14) into cantharidin proceeds with 47%3H-retention whereby the 11′-14C label is randomised at C-9 and C-11 in cantharidin and the ratio [2-14C]/[11′-14C] of (14) is retained indicating an intramolecular conversion of farnesol into cantharidin.

Key concepts: Farnesol, Cantharidin, Chemistry, Stereochemistry, Intramolecular force, Biochemistry, Organic chemistry

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Biosynthesis of cantharidin: evidence for the specific incorporation of C-4 and C-11? of farnesol — Research Paper | ScholarLens