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

Producción científica: Article › revisión exhaustiva

11 Citas (Scopus)

Resumen

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.

Idioma original	English
Páginas (desde-hasta)	2017-2033
Número de páginas	17
Publicación	Synthetic Communications
Volumen	19
N.º	11-12
DOI	https://doi.org/10.1080/00397918908052594
Estado	Published - jul 1 1989

Nota bibliográfica

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.

Financiación

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.

Financiadores	Número del financiador
National Institutes of Health (NIH)	GM 36256
University of Kentucky

ASJC Scopus subject areas

Organic Chemistry

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10.1080/00397918908052594

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@article{b83b9cafc5ef49138d84c22d0b1a6212,

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",

month = jul,

day = "1",

doi = "10.1080/00397918908052594",

language = "English",

volume = "19",

pages = "2017--2033",

number = "11-12",

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TY - JOUR

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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JO - Synthetic Communications

JF - Synthetic Communications

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ER -

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

Resumen

Nota bibliográfica

Financiación

ASJC Scopus subject areas

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Otros archivos y enlaces

Huella

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