Total Synthesis of (−)-Nakadomarin A

Total Synthesis of (−)-Nakadomarin A

The convergent synthesis of the polycyclic alkaloid (−)-nakadomarin A (1) is reported. The synthesis plan identified macrocyclic lactam 4 as one of the important synthons (eight steps). The other synthon (five steps) was bicyclo[6.3.0] lactam 5 containing a single stereocenter that controlled all of...

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Veröffentlicht in:Journal of the American Chemical Society 2013-06, Vol.135 (25), p.9338-9341
Hauptverfasser: Bonazzi, Simone, Cheng, Bichu, Wzorek, Joseph S, Evans, David A
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Sprache:eng
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Carbolines - chemical synthesis
Carbolines - chemistry
Crystallography, X-Ray
Models, Molecular
Molecular Conformation
Stereoisomerism
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container_issue 25
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container_title Journal of the American Chemical Society
container_volume 135
creator Bonazzi, Simone
Cheng, Bichu
Wzorek, Joseph S
Evans, David A
description The convergent synthesis of the polycyclic alkaloid (−)-nakadomarin A (1) is reported. The synthesis plan identified macrocyclic lactam 4 as one of the important synthons (eight steps). The other synthon (five steps) was bicyclo[6.3.0] lactam 5 containing a single stereocenter that controlled all of the subsequent stereochemistry during the assembly process. A silyl triflate-promoted cascade of 4 and 5 was used to assemble the bulk of the alkaloid skeleton with the exception of the C5–C6 bond. The nakadomarin synthesis was then completed in one additional step.
doi_str_mv 10.1021/ja404673s
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subjects Carbolines - chemical synthesis
Carbolines - chemistry
Crystallography, X-Ray
Models, Molecular
Molecular Conformation
Stereoisomerism
title Total Synthesis of (−)-Nakadomarin A
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