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Total synthesis of chaetoquadrins A-C.

Authors
  • Kim, U Bin
  • Furkert, Daniel P
  • Brimble, Margaret A
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Feb 01, 2013
Volume
15
Issue
3
Pages
658–661
Identifiers
DOI: 10.1021/ol303482k
PMID: 23327616
Source
Medline
License
Unknown

Abstract

The first total synthesis of the monoamine oxidase inhibitors chaetoquadrins A-C has been accomplished. Key steps in the synthesis include an aromatic Claisen rearrangement, asymmetric boron aldol reaction and acid-mediated spiroketalization. Comparison of spectral data for the synthetic spiroketals confirmed the proposed structure for these natural products.

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