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. 2009 Apr 2;11(7):1559-62.
doi: 10.1021/ol900173t.

Skeletally diverse small molecules using a build/couple/pair strategy

Takuya Uchida  1 , Manuela Rodriquez, Stuart L Schreiber
Affiliations

Skeletally diverse small molecules using a build/couple/pair strategy

Takuya Uchida et al. Org Lett. .

Abstract

Intermolecular couplings of simple building blocks using catalytic, stereoselective cross-Mannich reactions followed by intramolecular functional group-pairing reactions of easily accessed variants of the Mannich products are explored as a route to skeletally diverse small molecules. The synthetic pathway yields products having 12 different skeletons using only three steps and has the potential to enable substantial stereochemical diversification in the future.

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Figures

Scheme 1
Scheme 1. Build/Couple/Pair Strategy Yielding Skeletally Diverse Small Molecules
Scheme 2
Scheme 2. Cyclizations of N-Alkylated Intermediates
Scheme 3
Scheme 3. Cyclizations of N-Acylated Intermediates
Scheme 4
Scheme 4. Cyclizations of N-Acylaminoaldehyde Derivatives
Scheme 5
Scheme 5. Cyclizations of N-Acylaminoaldehyde Derivatives
See this image and copyright information in PMC

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