Journal article
Effect of C-9 Substituents on the Regioselectivity of A-Ring Reactions in Derivatives of the Wieland-Miescher Ketone
Journal of organic chemistry, Vol.59(21), pp.6313-6317
10/01/1994
DOI: 10.1021/jo00100a037
Abstract
The nature of C-9 substituents was found to have a significant influence on the regio-and stereochemistry of A-ring reactions in a variety of Wieland‒Miescher ketone derivatives. For example, Pd-catalyzed hydrogenation of the C-9 dioxolanes resulted in much better selectivity for the cis-fused products vis-a-vis the corresponding C-9 ketone, with the parent Wieland‒Miescher ketone itself and both C-4 methyl and C-4 carboalkoxy substituted analogues. In addition, methylation and acylation of A-ring enolates favored the C-2 isomer when a C-9 dioxolane group was present, but the C-4 substituted isomer was predominant with the corresponding C-9 ketone. These differences in regiochemistry may allow selective elaboration of cis-fused decalins during preparation of complex natural products. © 1994, American Chemical Society. All rights reserved.
Details
- Title: Subtitle
- Effect of C-9 Substituents on the Regioselectivity of A-Ring Reactions in Derivatives of the Wieland-Miescher Ketone
- Creators
- Kwangyong ParkWilliam J ScottDavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.59(21), pp.6313-6317
- Publisher
- American Chemical Society
- DOI
- 10.1021/jo00100a037
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Language
- English
- Date published
- 10/01/1994
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9984216666002771
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