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Published September 16, 2016 | Version Supplemental Material + Accepted Version
Journal Article Open

A Mild and General Larock Indolization Protocol for the Preparation of Unnatural Tryptophans

Creators

  • 1. ROR icon California Institute of Technology

Abstract

A mild and general protocol for the Pd(0)-catalyzed heteroannulation of o-bromoanilines and alkynes is described. Application of a Pd(0)/P(^tBu)_3 catalyst system enables the efficient coupling of o-bromoanilines at 60 °C, mitigating deleterious side reactions and enabling access to a broad range of useful unnatural tryptophans. The utility of this new protocol is demonstrated in the highly convergent total synthesis of the bisindole natural product (−)-aspergilazine A.

Additional Information

© 2016 American Chemical Society. Received: August 18, 2016; Publication Date (Web): September 6, 2016. We thank Dr. Scott Virgil of Caltech for helpful discussions, the Caltech Center for Catalysis and Chemical Synthesis for access to screening facilities and analytical equipment, and Sigma–Aldrich for a kind donation of chemicals. We gratefully acknowledge Jordan Beck and Lauren Chapman of Caltech for their assistance in the preparation of this manuscript. Fellowship support was provided by the National Science Foundation (Graduate Research Fellowship to M.E.K. and K.V.C., Grant No. DGE-1144469). S.E.R. is an American Cancer Society Research Scholar and a Heritage Medical Research Foundation investigator. Financial support from the NIH (NIGMS RGM097582A) and the donors of the ACS Petroleum Research Foundation is gratefully acknowledged. The authors declare no competing financial interest.

Attached Files

Accepted Version - nihms871735.pdf

Supplemental Material - ol6b02477_si_001.pdf

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Additional details

Identifiers

PMCID
PMC5505074
Eprint ID
70275
Resolver ID
CaltechAUTHORS:20160912-094332366

Funding

NSF Graduate Research Fellowship
DGE-1144469
American Cancer Society
Heritage Medical Research Institute
NIH
RGM097582A
American Chemical Society Petroleum Research Fund

Dates

Created
2016-09-12
Created from EPrint's datestamp field
Updated
2022-04-19
Created from EPrint's last_modified field

Caltech Custom Metadata

Caltech groups
Heritage Medical Research Institute