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 |
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Pages (from-to) | 2017-2033 |
Number of pages | 17 |
Journal | Synthetic Communications |
Volume | 19 |
Issue number | 11-12 |
DOIs | |
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