First synthesis of enantiopure 1,6-difunctionalized dodecahydrobenz[f] indenes

Jamie B. Scaglione; Nigam P. Rath; Douglas F. Covey

doi:10.1021/jo048561m

First synthesis of enantiopure 1,6-difunctionalized dodecahydrobenz[f] indenes

Jamie B. Scaglione
, Nigam P. Rath
, Douglas F. Covey

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

13 Scopus citations

Abstract

(Chemical Equation Presented) An enantiospecific route to the previously unreported 1,6-difunctionalized dodecahydrobenz[f]indene ring system is described. Optically pure Hajos - Parrish ketone is used as the building block for preparation of a 6-methyleneinden-5-ol. This allylic alcohol is then utilized in a Claisen rearrangement under Johnson's conditions to introduce a side chain that is further modified and cyclized to produce the benz[f]indene ring system.

Original language	English
Pages (from-to)	1089-1092
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	70
Issue number	3
DOIs	https://doi.org/10.1021/jo048561m
State	Published - Feb 4 2005

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abstract = "(Chemical Equation Presented) An enantiospecific route to the previously unreported 1,6-difunctionalized dodecahydrobenz[f]indene ring system is described. Optically pure Hajos - Parrish ketone is used as the building block for preparation of a 6-methyleneinden-5-ol. This allylic alcohol is then utilized in a Claisen rearrangement under Johnson's conditions to introduce a side chain that is further modified and cyclized to produce the benz[f]indene ring system.",

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AU - Rath, Nigam P.

AU - Covey, Douglas F.

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N2 - (Chemical Equation Presented) An enantiospecific route to the previously unreported 1,6-difunctionalized dodecahydrobenz[f]indene ring system is described. Optically pure Hajos - Parrish ketone is used as the building block for preparation of a 6-methyleneinden-5-ol. This allylic alcohol is then utilized in a Claisen rearrangement under Johnson's conditions to introduce a side chain that is further modified and cyclized to produce the benz[f]indene ring system.

AB - (Chemical Equation Presented) An enantiospecific route to the previously unreported 1,6-difunctionalized dodecahydrobenz[f]indene ring system is described. Optically pure Hajos - Parrish ketone is used as the building block for preparation of a 6-methyleneinden-5-ol. This allylic alcohol is then utilized in a Claisen rearrangement under Johnson's conditions to introduce a side chain that is further modified and cyclized to produce the benz[f]indene ring system.

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ER -

First synthesis of enantiopure 1,6-difunctionalized dodecahydrobenz[f] indenes

Abstract

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