Faraldos, Juan A., Kariuki, Benson ![]() |
Official URL: http://dx.doi.org/10.1021/ol1027893
Abstract
The enantiomeric 2-azapinanes, aza analogues of the pinyl carbocation intermediates in pinene biosynthesis, were synthesized from (−)- and (+)-cis-pinonic acids. The individual reactions in the 5-step sequence were Beckmann rearrangement of the pinonic acid oximes, cyclization to the N-acetyl lactams, hydrolysis to the NH-lactams, N-methylations, and LiAlH4 reductions. The anti stereochemistry of the N-methyl groups in the salts with respect to the gem-dimethyl bridge was established by NOE measurements and by X-ray diffraction analysis.
Item Type: | Article |
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Date Type: | Publication |
Status: | Published |
Schools: | Chemistry |
Subjects: | Q Science > QD Chemistry |
Publisher: | ACS |
ISSN: | 1523-7060 |
Last Modified: | 18 Oct 2022 14:01 |
URI: | https://orca.cardiff.ac.uk/id/eprint/16202 |
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