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. 2010 May 5;132(17):5926-7.
doi: 10.1021/ja101893b.

Total synthesis of (+)-complanadine A using an iridium-catalyzed pyridine C-H functionalization

Daniel F Fischer  1 , Richmond Sarpong
Affiliations

Total synthesis of (+)-complanadine A using an iridium-catalyzed pyridine C-H functionalization

Daniel F Fischer et al. J Am Chem Soc. .

Abstract

The total synthesis of the Lycopodium alkaloid complanadine A, which is an unsymmetrical dimer of lycodine, was achieved by exploiting a common tetracyclic precursor. Key to the success of the synthesis was the development of a late-stage site-selective C-H functionalization of a pyridine moiety to arrive at a key boronic ester intermediate.

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Figures

Figure 1
Figure 1
Selected Lycopodium alkaloids
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
Scheme 5
Scheme 5
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