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. 2009 May 7;11(9):1915-8.
doi: 10.1021/ol9003492.

Diastereoselective pyrrolidine synthesis via copper promoted intramolecular aminooxygenation of alkenes: formal synthesis of (+)-monomorine

Monissa C Paderes  1 , Sherry R Chemler
Affiliations

Diastereoselective pyrrolidine synthesis via copper promoted intramolecular aminooxygenation of alkenes: formal synthesis of (+)-monomorine

Monissa C Paderes et al. Org Lett. .

Abstract

The diastereoselectivity of the copper-promoted intramolecular aminooxygenation of various alkene substrates was investigated. Alpha-substituted 4-pentenyl sulfonamides favor the formation of 2,5-cis-pyrrolidines (dr >20:1) giving excellent yields which range from 76-97% while gamma-substituted substrates favor the 2,3-trans pyrrolidine adducts with moderate selectivity (ca. 3:1). A substrate whose N-substituent was directly tethered to the alpha-carbon exclusively yielded the 2,5-trans pyrrolidine. The synthetic utility of the method was demonstrated by a short and efficient formal synthesis of (+)-monomorine.

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Figures

Figure 1
Figure 1
Crystal structure of 31.
Scheme 1
Scheme 1
Copper(II) promoted diastereoselective formation of 2,5-cis-pyrrolidines and TEMPO trapping of radical intermediate.
Scheme 2
Scheme 2
Proposed mechanism for the formation of 2,5-cis-pyrrolidine.
Scheme 3
Scheme 3
Formal synthesis of (+)-monomorine.
Scheme 4
Scheme 4
Diastereoselective aminooxygenation of sulfonamide 29 forming the trans pyrrolidine 31.
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References

    1. Lewis JR. Nat. Prod. Rep. 2001;18:95–128. - PubMed
    2. O’Hagan D. Nat. Prod. Rep. 2000;17:435–446. - PubMed
    1. Nash RJ, Fellows LE, Dring JV, Fleet GWJ, Derome AE, Hamor TA, Scofield AM, Watkin DJ. Tetrahedron Lett. 1988;29:2487–2490.
    2. Scofield AM, Rossiter JT, Witham P, Kite GC, Nash RJ, Fellows LE. Phytochemistry. 1990;29:107–109.
    1. Kato A, Kano E, Adachi I, Molyneux RJ, Watson AA, Nash RJ, Fleet GWJ, Wormald MR, Kizu H, Ikeda K, Asano N. Tetrahedron: Asymmetry. 2003;14:325–331.
    2. Molyneux RJ, Benson M, Wong RY, Tropea JE, Elbein AD. J. Nat. Prod. 1988;51:1198–1206.
    1. Kinzy TG, Harger JW, Carr-Schmid A, Kwon J, Shastry M, Justice M, Dinman JD. Virology. 2002;300:60–70. - PubMed
    2. Achenbach TV, Slater PE, Brummerhop H, Bach T, Müller R. Antimicrob. Agents Chemother. 2000;44:2794–2801. - PMC - PubMed
    1. Powell RG, Weisleder D, Smith CR, Jr, Rohwedder WK. Tetrahedron Lett. 1970;11:815–818. - PubMed

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