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

46 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",

month = jan,

doi = "10.1021/ja00179a038",

language = "English",

volume = "112",

pages = "8490--8496",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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T1 - Total Synthesis of (±)-Dactylol and Related Studies

AU - Feldman, Ken S.

AU - Wu, Ming Jung

AU - Rotella, David P.

PY - 1990/1

Y1 - 1990/1

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.

UR - https://www.scopus.com/pages/publications/0001135598

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DO - 10.1021/ja00179a038

M3 - Article

AN - SCOPUS:0001135598

SN - 0002-7863

VL - 112

SP - 8490

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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