Palladium-catalyzed potassium enoxyborate alkylation of enantiopure Hajos-Parrish indenone to construct rearranged steroid ring systems

Izabella Jastrzebska; Jamie B. Scaglione; Gregory T. DeKoster; Nigam P. Rath; Douglas F. Covey

doi:10.1021/jo070530e

Palladium-catalyzed potassium enoxyborate alkylation of enantiopure Hajos-Parrish indenone to construct rearranged steroid ring systems

Izabella Jastrzebska, Jamie B. Scaglione, Gregory T. DeKoster, Nigam P. Rath, Douglas F. Covey

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

19 Scopus citations

Abstract

(Chemical Equation Presented) Here we report the stereo- and regiospecific C-6 alkylation of a trans-inden-5-one (from optically pure Hajos-Parrish ketone) with allylic electrophiles. Use of this alkylation procedure has led to an improved synthesis of the benz[f]indene ring system and the first enantiospecific total syntheses of the cyclopenta-[b]anthracene and cyclopenta[b]phenanthrene ring systems (two synthetic routes).

Original language	English
Pages (from-to)	4837-4843
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	72
Issue number	13
DOIs	https://doi.org/10.1021/jo070530e
State	Published - Jun 22 2007

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title = "Palladium-catalyzed potassium enoxyborate alkylation of enantiopure Hajos-Parrish indenone to construct rearranged steroid ring systems",

abstract = "(Chemical Equation Presented) Here we report the stereo- and regiospecific C-6 alkylation of a trans-inden-5-one (from optically pure Hajos-Parrish ketone) with allylic electrophiles. Use of this alkylation procedure has led to an improved synthesis of the benz[f]indene ring system and the first enantiospecific total syntheses of the cyclopenta-[b]anthracene and cyclopenta[b]phenanthrene ring systems (two synthetic routes).",

author = "Izabella Jastrzebska and Scaglione, {Jamie B.} and DeKoster, {Gregory T.} and Rath, {Nigam P.} and Covey, {Douglas F.}",

year = "2007",

month = jun,

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doi = "10.1021/jo070530e",

language = "English",

volume = "72",

pages = "4837--4843",

journal = "Journal of Organic Chemistry",

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T1 - Palladium-catalyzed potassium enoxyborate alkylation of enantiopure Hajos-Parrish indenone to construct rearranged steroid ring systems

AU - Jastrzebska, Izabella

AU - Scaglione, Jamie B.

AU - DeKoster, Gregory T.

AU - Rath, Nigam P.

AU - Covey, Douglas F.

PY - 2007/6/22

Y1 - 2007/6/22

N2 - (Chemical Equation Presented) Here we report the stereo- and regiospecific C-6 alkylation of a trans-inden-5-one (from optically pure Hajos-Parrish ketone) with allylic electrophiles. Use of this alkylation procedure has led to an improved synthesis of the benz[f]indene ring system and the first enantiospecific total syntheses of the cyclopenta-[b]anthracene and cyclopenta[b]phenanthrene ring systems (two synthetic routes).

AB - (Chemical Equation Presented) Here we report the stereo- and regiospecific C-6 alkylation of a trans-inden-5-one (from optically pure Hajos-Parrish ketone) with allylic electrophiles. Use of this alkylation procedure has led to an improved synthesis of the benz[f]indene ring system and the first enantiospecific total syntheses of the cyclopenta-[b]anthracene and cyclopenta[b]phenanthrene ring systems (two synthetic routes).

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U2 - 10.1021/jo070530e

DO - 10.1021/jo070530e

M3 - Article

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SN - 0022-3263

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EP - 4843

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 13

ER -

Palladium-catalyzed potassium enoxyborate alkylation of enantiopure Hajos-Parrish indenone to construct rearranged steroid ring systems

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