AI Article Synopsis
- The synthesis utilizes inexpensive (+)-pulegone as a chiral building block to create complex diquinane structures like (+)-paniculatine, (-)-magellanine, and (+)-magellaninone.
- Key techniques in this synthesis include tandem acylation-alkylation, along with palladium-catalyzed reactions for building the tetracyclic framework.
- This method is notably efficient, requiring only 12-14 steps, making it the shortest synthesis route reported so far.
Article Abstract
Starting from inexpensive (+)-pulegone as the chiral building block, a highly convergent synthesis of the unusual diquinane-based structures of (+)-paniculatine (1), (-)-magellanine (2), and (+)-magellaninone (3), has been achieved. This approach is based upon a tandem acylation-alkylation of ketoester 8 and palladium-catalyzed olefin insertion, oxidation, and hydrogenation for construction of the tetracyclic framework. This exceedingly concise strategy, requiring only 12-14 steps, is the shortest to date.
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| http://dx.doi.org/10.1021/acs.orglett.5b01975 | DOI Listing |
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