Hydroboration of tricarbonylironergosteryl benzoate. Synthesis of (22R)- and (22S)-3β-benzoyloxyergosta-5,7-dien-22-ol and (23R)-3β- benzoyloxyergosta-5,7-dien-23-ol

Leslie Gunatilaka, A. Fernandez Mateos

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2 Citations (Scopus)

Abstract

Hydration of tricarbonylironergosteryl benzoate via hydroboration and subsequent decomplexing affords a mixture of (22R)- and (22S)-3β- benzoyloxyergosta-5,7-dien-22-ol and (23R)-3β-benzoyloxyergosta-5,7-dien- 23-ol. Oxidation gives 3β-benzoyloxyergosta-5,7-dien-22- and -23-one. On reduction these ketones yield (23S)-3β-benzoyloxyergosta-5,7-dien-23-ol in addition to the above three dienols. Stereochemical assignments are on the basis of molecular rotations.

Original languageEnglish (US)
Pages (from-to)935-938
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
StatePublished - 1979
Externally publishedYes

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Benzoates
Ketones
Hydration
Oxidation

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Hydroboration of tricarbonylironergosteryl benzoate. Synthesis of (22R)- and (22S)-3β-benzoyloxyergosta-5,7-dien-22-ol and (23R)-3β- benzoyloxyergosta-5,7-dien-23-ol",
abstract = "Hydration of tricarbonylironergosteryl benzoate via hydroboration and subsequent decomplexing affords a mixture of (22R)- and (22S)-3β- benzoyloxyergosta-5,7-dien-22-ol and (23R)-3β-benzoyloxyergosta-5,7-dien- 23-ol. Oxidation gives 3β-benzoyloxyergosta-5,7-dien-22- and -23-one. On reduction these ketones yield (23S)-3β-benzoyloxyergosta-5,7-dien-23-ol in addition to the above three dienols. Stereochemical assignments are on the basis of molecular rotations.",
author = "Leslie Gunatilaka and {Fernandez Mateos}, A.",
year = "1979",
language = "English (US)",
pages = "935--938",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
issn = "1472-7781",
publisher = "Chemical Society",

}

TY - JOUR

T1 - Hydroboration of tricarbonylironergosteryl benzoate. Synthesis of (22R)- and (22S)-3β-benzoyloxyergosta-5,7-dien-22-ol and (23R)-3β- benzoyloxyergosta-5,7-dien-23-ol

AU - Gunatilaka, Leslie

AU - Fernandez Mateos, A.

PY - 1979

Y1 - 1979

N2 - Hydration of tricarbonylironergosteryl benzoate via hydroboration and subsequent decomplexing affords a mixture of (22R)- and (22S)-3β- benzoyloxyergosta-5,7-dien-22-ol and (23R)-3β-benzoyloxyergosta-5,7-dien- 23-ol. Oxidation gives 3β-benzoyloxyergosta-5,7-dien-22- and -23-one. On reduction these ketones yield (23S)-3β-benzoyloxyergosta-5,7-dien-23-ol in addition to the above three dienols. Stereochemical assignments are on the basis of molecular rotations.

AB - Hydration of tricarbonylironergosteryl benzoate via hydroboration and subsequent decomplexing affords a mixture of (22R)- and (22S)-3β- benzoyloxyergosta-5,7-dien-22-ol and (23R)-3β-benzoyloxyergosta-5,7-dien- 23-ol. Oxidation gives 3β-benzoyloxyergosta-5,7-dien-22- and -23-one. On reduction these ketones yield (23S)-3β-benzoyloxyergosta-5,7-dien-23-ol in addition to the above three dienols. Stereochemical assignments are on the basis of molecular rotations.

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JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

SN - 1472-7781

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