Effect of C-9 Substituents on the Regioselectivity of A-Ring Reactions in Derivatives of the Wieland‒Miescher Ketone
- Authors
- Park, Kwangyong; Scott, William J.; Wiemer, David F.
- Issue Date
- Oct-1994
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.59, no.21, pp 6313 - 6317
- Pages
- 5
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 59
- Number
- 21
- Start Page
- 6313
- End Page
- 6317
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/29613
- DOI
- 10.1021/jo00100a037
- ISSN
- 0022-3263
1520-6904
- 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-funded 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.
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