Synthetic and stereochemical studies directed towards anatoxin-a
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- Vol. 22 (1) , 145-155
- https://doi.org/10.1039/p19910000145
Abstract
The synthesis and stereocontrolled AgI-catalysed cyclisation of a series of allenic amino esters 8a–e is described. For compounds 8a–d the cis-2,5-disubstituted pyrrolidine 9 is formed exclusively but the primary amine 8e undergoes cyclisation nonselectively to give a mixture of cis- and trans-pyrrolidines 9e and 10e. The synthetic potential of this allene-based methodology has been illustrated by the conversion of compound 8avia9a into (±)-anatoxin-a 1 and the methoxy phosphine oxides 18 and 19 have been studied as ketone homologating agents within this context. The enzymatic resolution of (±)-8a using chymotrypsin is also described.Keywords
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