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Enantioselective Total Synthesis of (+)-Jungermatrobrunin A.
- Source :
-
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2019 Aug 05; Vol. 58 (32), pp. 10879-10883. Date of Electronic Publication: 2019 Jul 03. - Publication Year :
- 2019
-
Abstract
- A concise and enantioselective total synthesis of (+)-jungermatrobrunin A (1), which features a unique bicyclo[3.2.1]octene ring skeleton with an unprecedented peroxide bridge, was accomplished in 13 steps by making use of a late-stage visible-light-mediated Schenck ene reaction of (-)-1α,6α-diacetoxyjungermannenone C (2). Along the way, a UV-light-induced bicyclo[3.2.1]octene ring rearrangement afforded (+)-12-hydroxy-1α,6α-diacetoxy-ent-kaura-9(11),16-dien-15-one (4). These divergent photo-induced skeletal rearrangements support a possible biogenetic relationship between (+)-1, (-)-2, and (+)-4.<br /> (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Details
- Language :
- English
- ISSN :
- 1521-3773
- Volume :
- 58
- Issue :
- 32
- Database :
- MEDLINE
- Journal :
- Angewandte Chemie (International ed. in English)
- Publication Type :
- Academic Journal
- Accession number :
- 31056826
- Full Text :
- https://doi.org/10.1002/anie.201903682