Enantioselective Total Synthesis of (-)-Lansai B and (+)-Nocardioazines A and B

Creators: Wang, Haoxuan; Reisman, Sarah E.

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Abstract

The concise total syntheses of the bis(pyrroloindolines) (−)-lansai B and (+)- nocardioazines A and B are reported. The key pyrroloindoline building blocks are rapidly prepared by enantioselective formal [3+2] cycloaddition reactions. The macrocycle of (+)-nocardioazine A is constructed by an unusual intramolecular diketopiperazine formation.

Additional Information

© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Article first published online: 28 Apr. 2014. We thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment, as well as Materia, Inc. and Sigma–Aldrich for kind donations of chemicals. We are grateful to Dr. David VanderVelde for assistance with NMR structure analysis, and Mr. Larry Henling for X-ray structure determination. The Bruker KAPPA APEXII X-ray diffractometer was purchased with an NSF Chemistry Research Instrumentation award to Caltech (CHE-0639094). NMR spectra were obtained on a spectrometer funded by the NIH (RR027690). S.E.R. is a fellow of the Alfred P. Sloan Foundation, a Camille Dreyfus Teacher-Scholar, and an American Cancer Society Research Scholar. Financial support from the California Institute of Technology, the NIH (NIGMS RGM097582A, and DuPont is gratefully acknowledged.

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