Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 7, Pages 1539-1543Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201706057
Keywords
alkaloids; asymmetric synthesis; Dieckmann condensation; total synthesis; ynolate; pyrrolo[1,2-a]azepine core
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Funding
- JSPS KAKENHI Grant [JP22390002, JP24106731, JP16H01157, JP26293004, JP17K14449]
- Science and Technology Research Promotion Program for Agriculture, Forestry, Fisheries and Food industry
- MEXT Project of Integrated Research Consortium on Chemical Sciences
- Grants-in-Aid for Scientific Research [16H01157] Funding Source: KAKEN
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The first asymmetric total synthesis of (-)-stemonamine is described. The key reactions included intramolecular acylation to construct the seven-membered ring and a tandem [2+2] cycloaddition-Dieckmann condensation reaction using an ynolate to form the fully substituted cyclopentenone moiety. Racemization and epimerization of the natural product were first experimentally demonstrated.
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