Total Synthesis of (±)-Dactylol and Related Studies

Ken S. Feldman; Ming Jung Wu; David P. Rotella

doi:10.1021/ja00179a038

Total Synthesis of (±)-Dactylol and Related Studies

Ken S. Feldman, Ming Jung Wu, David P. Rotella

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

45 Scopus citations

Abstract

The marine sesquiterpene (±)-dactylol was prepared from 2,5-dimethyl-7-(3-methyl-4-pentenyl)tropone in six steps. Salient features of the synthesis include; (1) a stereo-and regioselective intramolecular tropone-alkene [6π + 2π] photocyclization to furnish the dactylol carbocyclic skeleton, (2) a regioselective Baeyer-Villiger oxidation of a bisneopentyl ketone, and (3) a chemoselective 1,4-reduction of a cyclocta-1,3-diene moiety.

Original language	English
Pages (from-to)	8490-8496
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	112
Issue number	23
DOIs	https://doi.org/10.1021/ja00179a038
State	Published - Jan 1990

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title = "Total Synthesis of (±)-Dactylol and Related Studies",

abstract = "The marine sesquiterpene (±)-dactylol was prepared from 2,5-dimethyl-7-(3-methyl-4-pentenyl)tropone in six steps. Salient features of the synthesis include; (1) a stereo-and regioselective intramolecular tropone-alkene [6π + 2π] photocyclization to furnish the dactylol carbocyclic skeleton, (2) a regioselective Baeyer-Villiger oxidation of a bisneopentyl ketone, and (3) a chemoselective 1,4-reduction of a cyclocta-1,3-diene moiety.",

author = "Feldman, {Ken S.} and Wu, {Ming Jung} and Rotella, {David P.}",

year = "1990",

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doi = "10.1021/ja00179a038",

language = "English",

volume = "112",

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AU - Feldman, Ken S.

AU - Wu, Ming Jung

AU - Rotella, David P.

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N2 - The marine sesquiterpene (±)-dactylol was prepared from 2,5-dimethyl-7-(3-methyl-4-pentenyl)tropone in six steps. Salient features of the synthesis include; (1) a stereo-and regioselective intramolecular tropone-alkene [6π + 2π] photocyclization to furnish the dactylol carbocyclic skeleton, (2) a regioselective Baeyer-Villiger oxidation of a bisneopentyl ketone, and (3) a chemoselective 1,4-reduction of a cyclocta-1,3-diene moiety.

AB - The marine sesquiterpene (±)-dactylol was prepared from 2,5-dimethyl-7-(3-methyl-4-pentenyl)tropone in six steps. Salient features of the synthesis include; (1) a stereo-and regioselective intramolecular tropone-alkene [6π + 2π] photocyclization to furnish the dactylol carbocyclic skeleton, (2) a regioselective Baeyer-Villiger oxidation of a bisneopentyl ketone, and (3) a chemoselective 1,4-reduction of a cyclocta-1,3-diene moiety.

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EP - 8496

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 23

ER -

Total Synthesis of (±)-Dactylol and Related Studies

Abstract

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