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

A. A. Leslie Gunatilaka; A. Fernandez Mateos

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

A. A. Leslie Gunatilaka
, A. Fernandez Mateos

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

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 language	English (US)
Pages (from-to)	935-938
Number of pages	4
Journal	Journal of the Chemical Society, Perkin Transactions 1
State	Published - 1979
Externally published	Yes

ASJC Scopus subject areas

General Chemistry

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\}, \{A. A.\} 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 - Leslie Gunatilaka, A. A.

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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UR - https://www.scopus.com/pages/publications/37049103544#tab=citedBy

M3 - Article

AN - SCOPUS:37049103544

SN - 1472-7781

SP - 935

EP - 938

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

ER -

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

ASJC Scopus subject areas

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