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Total Synthesis of the Akuammiline Alkaloid (±)-Vincorine

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Department of Chemistry of Medicinal Natural Products, Key Laboratory of Drug Targeting and Novel Delivery System of Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041, P. R. China
Cite this: J. Am. Chem. Soc. 2009, 131, 16, 6013–6020
Publication Date (Web):March 27, 2009
https://doi.org/10.1021/ja901219v
Copyright © 2009 American Chemical Society

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    Abstract

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    The first total synthesis of the akuammiline alkaloid (±)-vincorine (6) has been accomplished in about 1% overall yield in 31 steps. A concise assembly of the core 1,2-disubstituted 1,2,3,4-tetrahydro-4a,9a-iminoethanocarbazole (1), a distinctive feature of akuammiline and strychnos alkaloids, was developed via a three-step one-pot cascade reaction consisting of copper-catalyzed intramolecular cyclopropanation, ring-opening, and ring closure. The construction of the last seven-membered E-ring in a rigid two-ring moiety (31, 45 to 47) through Heck coupling, Michael addition, π-allyl/Heck or π-allyl/Stille coupling failed, leading us to seek an alternative method. After successful addition of an acetate side chain on C15 of the cyclohexenyl ring (D-ring) in Boc-protected 35b by a Johnson−Claisen rearrangement and multistep modification of the functionality in the rearrangement product 33a, the E-ring formation was then realized for providing pentacyclic lactam 32 through intramolecular condensation of the acid group on the D-ring and the amine group on the C-ring with Mukaiyama’s reagent. An E-ethylidenyl group on the E-ring was stereoselectively added to afford lactam 56a through a two-step reaction of 32 consisting of aldol addition with acetaldehyde and cis-elimination of the resulting hydroxyl group. Final elaboration of 56a, including opening of the seven-membered E-ring, selective reduction of the α,β-unsaturated ester, and reclosure of the seven-membered E-ring completed the total synthesis of 6.

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    Experimental procedures, spectroscopic analytical data for all new compounds, and CIF files of crystallographic information for compound 32. This material is available free of charge via the Internet at http://pubs.acs.org.

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