Synthesis of 3,4,4a,5,6,7,8,8aa-octahydro-4a0,8a-dimethyl-2(1h)-naphthalenones from the wieland-miescher ketone

Moonsun Kim; Kenji Kawada; David S. Watt

doi:10.1080/00397918908052594

Synthesis of 3,4,4a,5,6,7,8,8aa-octahydro-4a0,8a-dimethyl-2(1h)-naphthalenones from the wieland-miescher ketone

Moonsun Kim, Kenji Kawada, David S. Watt

Molecular and Cellular Biochemistry

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

11 Scopus citations

Abstract

Conversion of the Wieland-Miescher ketone to a bicyclic dienophile capable of providing the AB rings of the picrasane skeleton of the guassinoids required the introduction of a C-8a methyl group in a 2-decalone. Among the routes explored, the conversion of the Wieland-Miescher ketone to a 4,4a,5,6,7,8-hexa-hydro-4ap-methyl-8-methylene-2(3H)-napthalenone and subsequent reduction to a 3,4,4a,5,6,7,8,8aa-octahydro-4a0,8a-dimethyl-2(lH)-napthalenone proved most useful.

Original language	English
Pages (from-to)	2017-2033
Number of pages	17
Journal	Synthetic Communications
Volume	19
Issue number	11-12
DOIs	https://doi.org/10.1080/00397918908052594
State	Published - Jul 1 1989

Bibliographical note

Funding Information:
Acknowledgement We thank the National Institutes of Health (GM 36256) for their generous financial support and the University of Kentucky for the purchase of Bond Issue Equipment.

ASJC Scopus subject areas

Organic Chemistry

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10.1080/00397918908052594

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title = "Synthesis of 3,4,4a,5,6,7,8,8aa-octahydro-4a0,8a-dimethyl-2(1h)-naphthalenones from the wieland-miescher ketone",

abstract = "Conversion of the Wieland-Miescher ketone to a bicyclic dienophile capable of providing the AB rings of the picrasane skeleton of the guassinoids required the introduction of a C-8a methyl group in a 2-decalone. Among the routes explored, the conversion of the Wieland-Miescher ketone to a 4,4a,5,6,7,8-hexa-hydro-4ap-methyl-8-methylene-2(3H)-napthalenone and subsequent reduction to a 3,4,4a,5,6,7,8,8aa-octahydro-4a0,8a-dimethyl-2(lH)-napthalenone proved most useful.",

author = "Moonsun Kim and Kenji Kawada and Watt, {David S.}",

note = "Funding Information: Acknowledgement We thank the National Institutes of Health (GM 36256) for their generous financial support and the University of Kentucky for the purchase of Bond Issue Equipment.",

year = "1989",

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doi = "10.1080/00397918908052594",

language = "English",

volume = "19",

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T1 - Synthesis of 3,4,4a,5,6,7,8,8aa-octahydro-4a0,8a-dimethyl-2(1h)-naphthalenones from the wieland-miescher ketone

AU - Kim, Moonsun

AU - Kawada, Kenji

AU - Watt, David S.

N1 - Funding Information: Acknowledgement We thank the National Institutes of Health (GM 36256) for their generous financial support and the University of Kentucky for the purchase of Bond Issue Equipment.

PY - 1989/7/1

Y1 - 1989/7/1

N2 - Conversion of the Wieland-Miescher ketone to a bicyclic dienophile capable of providing the AB rings of the picrasane skeleton of the guassinoids required the introduction of a C-8a methyl group in a 2-decalone. Among the routes explored, the conversion of the Wieland-Miescher ketone to a 4,4a,5,6,7,8-hexa-hydro-4ap-methyl-8-methylene-2(3H)-napthalenone and subsequent reduction to a 3,4,4a,5,6,7,8,8aa-octahydro-4a0,8a-dimethyl-2(lH)-napthalenone proved most useful.

AB - Conversion of the Wieland-Miescher ketone to a bicyclic dienophile capable of providing the AB rings of the picrasane skeleton of the guassinoids required the introduction of a C-8a methyl group in a 2-decalone. Among the routes explored, the conversion of the Wieland-Miescher ketone to a 4,4a,5,6,7,8-hexa-hydro-4ap-methyl-8-methylene-2(3H)-napthalenone and subsequent reduction to a 3,4,4a,5,6,7,8,8aa-octahydro-4a0,8a-dimethyl-2(lH)-napthalenone proved most useful.

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Synthesis of 3,4,4a,5,6,7,8,8aa-octahydro-4a0,8a-dimethyl-2(1h)-naphthalenones from the wieland-miescher ketone

Abstract

Bibliographical note

ASJC Scopus subject areas

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