Journal of Organic Chemistry p. 3887 - 3891 (1981)
Update date:2022-08-05
Topics:
Wilson, Stephen R.
Sawicki, Robert A.
Huffman, J. C.
Application of transannular cyclizations to the synthesis of bridged pyrrolizidine alkaloids such as loline (1) is described.The general method involves bromination of 3-aza-9-oxabicyclo<4.2.1>non-7-ene (5), leading directly to the skeleton (12a) of the lolium alkaloids.Unsuccessful attempts to replace the bromine are described.The X-ray structure of the synthetic compound 12a as well as loline itself (1) and the biogenesis of lolium alkaloids are also discussed.
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(1949)
