AI Article Synopsis
- A stereocontrolled total synthesis of (-)-stemoamide starts from (S)-pyroglutaminol and involves several key intermediate steps.
- The synthesis utilizes chemoselective iodoboration and a Pd(0)-catalyzed Negishi cross-coupling to create significant intermediates, followed by a ring-closing metathesis reaction.
- The final product's specific C8-C9 trans-stereochemistry is achieved through a stereoselective bromolactonization process followed by 1,4-reduction.
Article Abstract
A stereocontrolled total synthesis of (-)-stemoamide (1) is presented. The synthesis starts from commercially available (S)-pyroglutaminol (4). A chemoselective iodoboration of 5 was used to access key intermediate 3. The beta,gamma-unsaturated azepine derivative 2 was obtained via a Pd(0)-catalyzed sp(2)-sp(3) Negishi cross-coupling using a Reformatsky nucleophile followed by a ring-closing metathesis reaction. The required C8-C9 trans-stereochemistry of 1 was accessed through a stereoselective bromolactonization/1,4-reduction sequence.
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| http://dx.doi.org/10.1021/jo070498o | DOI Listing |
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