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

Research output: Contribution to journalArticlepeer-review

4 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 languageEnglish
Pages (from-to)2017-2033
Number of pages17
JournalSynthetic Communications
Volume19
Issue number11-12
DOIs
StatePublished - 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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