The Synthesis of Some Lactones Related to the Cardiac Aglycones
β Scribed by Conine, James W. ;Jones, James W.
- Publisher
- Elsevier
- Year
- 1954
- Weight
- 374 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0095-9553
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π SIMILAR VOLUMES
The synthesis and crystallographic analysis of a bicyclic core related to the esperamicin/ calichemicin aglycones is reported. A key reaction involves the skeletal rearrangement of a mesylate derived from a type II Diels-Alder cycloadduct.
Five 16Ξ±,17Ξ±-oxido-steroids were subjected to acids, bases and lithium hydroperoxide. Acids caused Wagner-Meerwein-type rearrangement irrespective of the side-chain structure. The 16Ξ±,17Ξ±-epoxides proved resistant to bases unless a C( 22)\_O group was present; in the case of 22-esters or 22-ketones
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