Abstract
A chiral synthesis of the Sceletium alkaloid (-)-mesembranol 1 is described. The cyclohexane ring in 1 is prepared in an optically active form from D-glucose using Ferrier's carbocyclisation, and the critical stereochemistry of the quaternary carbon in 1 is constructed stereoselectively via chirality transfer by way of Claisen rearrangement of the cyclohexenol derivative 14a. The perhydroindole skeleton in 1 is effectively generated by intramolecular aminomercuriation of the amino-olefin 18.
Original language | English |
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Pages (from-to) | 275-280 |
Number of pages | 6 |
Journal | Journal of the Chemical Society - Perkin Transactions 1 |
Issue number | 3 |
DOIs | |
Publication status | Published - 1997 Feb 7 |
ASJC Scopus subject areas
- Chemistry(all)