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Synfacts 2022; 18(08): 0837
DOI: 10.1055/s-0041-1738237
DOI: 10.1055/s-0041-1738237
Synthesis of Natural Products and Potential Drugs
Synthesis of (±)-Longifolene
Oppolzer W,
*,
Godel T.
Université de Genève, Switzerland
A New and Efficient Total Synthesis of (±)-Longifolene.
J. Am. Chem. Soc. 1978;
100: 2583-2584
DOI: 10.1021/ja00476a071.
A New and Efficient Total Synthesis of (±)-Longifolene.
J. Am. Chem. Soc. 1978;
100: 2583-2584
DOI: 10.1021/ja00476a071.
Key words
(±)-longifolene - sesquiterpenes - de Mayo reaction - Simmons–Smith cyclopropanation - enamine acylation
Significance
Oppolzer and Godel highlighted the synthetic utility of the de Mayo reaction sequence in their classical synthesis of longifolene. This tricyclic sesquiterpene occurs in the resin of several Pinus species, commonly extracted from its namesake Pinus longifolia, and is valued for its woody odor.
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Comment
[2+2] Photocycloaddition of enone D and hydrogenolysis of the Cbz group from the ensuing cyclobutanol E leads to retro-aldol fragmentation, completing the de Mayo sequence. This rapid approach forges the longifolene skeleton F in only four steps and 50% overall yield.
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Publication History
Article published online:
18 July 2022
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