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ChemInform Abstract: Synthetic Studies Towards Novel Tetracyclic Lycopodium Alkaloids: A Synthesis of Deoxymagellaninone.

✍ Scribed by G. MEHTA; M. S. REDDY; A. THOMAS


Publisher
John Wiley and Sons
Year
2010
Weight
40 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis


Synthetic Studies Towards Novel Tetracyclic Lycopodium Alkaloids:

A Synthesis of Deoxymagellaninone.

-A novel, linear triquinanebased strategy directed towards the synthesis of tetracyclic alkaloids of the paniculatine and magellanine type is presented and applied to the preparation of deoxymagellaninone (XVII). The synthesis involves the 'carbocycle-heterocycle equivalency' strategy for the introduction of the N-methylpiperidine ring (D) from a cyclopentene precursor. Construction of the cyclohexane ring (A) with the correct stereochemistry is achieved via butenylation of linear triquinane (IV) and intramolecular Michael addition of the derived methylcarbonyl compound (VIII) or alternatively, a cationic enone-olefin cyclization. -(MEHTA, G.;


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