Synthesis of the spirosesquiterpene (−)-acorenone and related cyclopentanoid monoterpenes | Zendy

Gordon L. Lange | Zendy; Eli Neidert | Zendy; Will J. Orrom | Zendy; David Wallace | Zendy

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Synthesis of the spirosesquiterpene (−)-acorenone and related cyclopentanoid monoterpenes

Author(s) -

Gordon L. Lange,

Eli Neidert,

Will J. Orrom,

David Wallace

Publication year - 1978

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v78-266

Subject(s) - chemistry , aldehyde , yield (engineering) , ketone , enamine , acetic acid , organic chemistry , alcohol , benzene , iodide , monoterpene , optically active , total synthesis , catalysis , materials science , metallurgy

The first total synthesis of the spirosesquiterpene (−)-acorenone (1) is described. The critical step involves a spiroannelation of the enamine of aldehyde 11 with 1-methoxy-3-buten-2-one (16) in the presence of acetic acid to give ketone 17. Reaction of 17 with methylmagnesium iodide followed by treatment of the resultant alcohol 18 with p-toluenesulfonic acid in refluxing benzene leads directly to 1 in good overall yield. As the starting material for the preparation of the cyclopentanoid aldehyde 11 was (+)-limonene the final product is optically active and thus the absolute configuration of naturally occurring (−)-acorenone (1) is established. The preparation of a number of other optically active cyclopentanoid monoterpenes (4 and 13) is also described.

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