Abstract
Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R)CHCH2 and allylation, or acylation with but-3-enoic acid, followed by ring-closing metathesis resulted in the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anisomycin (R = p-MeOC6H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.
Original language | English |
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Pages (from-to) | 5833-5836 |
Number of pages | 4 |
Journal | Organometallics |
Volume | 28 |
Issue number | 19 |
DOIs | |
Publication status | Published - 2009 |