Total Synthesis of (±)‐Quebrachamine via [3+2] Cycloaddition and Efficient Chloroacetamide Photocyclization | Zendy

Bajtos Barbora | Zendy; Pagenkopf Brian L. | Zendy

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Total Synthesis of (±)‐Quebrachamine via [3+2] Cycloaddition and Efficient Chloroacetamide Photocyclization

Author(s) -

Bajtos Barbora,

Pagenkopf Brian L.

Publication year - 2009

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200801154

Subject(s) - chemistry , cycloaddition , nitrile , cyclopropane , total synthesis , ring (chemistry) , yield (engineering) , indole test , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , materials science , metallurgy

The total synthesis of (±)‐quebrachamine has been completed in 13 linear steps and 17.8 % overall yield. The indole core was constructed via a formal [3+2] dipolar cycloaddition between a functionalized nitrile and donor‐acceptor cyclopropane, and the synthetically challenging nine‐membered ring was secured by an efficient chloroacetamide photocyclization.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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