The Alkaloids of Rauwolfia Serpentina Benth*

Phillips, Donald D.; Chadha, M. S.

doi:10.1002/jps.3030440912

Cited by 18 publications

(1 citation statement)

References 139 publications

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“…A general solution to this problem would yield a strategy for the preparation of the yohimbinoid alkaloids, given that structures in this class vary in the substitution about the indole moiety (see 4-13 , Figure 1), and include several members that are epimeric at C(3). 22,23,24,25,26,27 Herein, we disclose our efforts toward a general synthesis of the D/E cis-fused members of the yohimbinoid alkaloid family (i.e., 8-13 , Figure 1). This approach is showcased in the first total syntheses of the C(3) epimeric natural products venenatine ( 9 ) and alstovenine ( 12 ) in racemic form.…”

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A divergent approach to the synthesis of the yohimbinoid alkaloids venenatine and alstovenine

et al. 2012

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The yohimbinoid alkaloids have received considerable attention from the synthetic community due to their interesting chemical structures and varied biological activity. Although there have been several elegant syntheses of certain members of this group of alkaloids, a truly unified approach has yet to be developed. In short, general approaches to this compound class have been hampered by a lack of complete control in setting the C(3) stereocenter at a late stage. Herein, we report that a functionalized hydrindanone enables a divergent strategy that builds on precedent from Stork, which addresses this long standing challenge. Utilizing an aminonitrile intermediate, the stereochemistry at C(3) of the yohimbinoid skeleton can be effectively controlled in a Pictet-Spengler reaction. This approach has been applied to the first total syntheses of the C(3) epimeric natural products venenatine and alstovenine.

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confidence: 99%