Details
| Original language | English |
|---|---|
| Pages (from-to) | 1222-1226 |
| Number of pages | 5 |
| Journal | Journal of the American Chemical Society |
| Volume | 141 |
| Issue number | 3 |
| Early online date | 7 Jan 2019 |
| Publication status | Published - 23 Jan 2019 |
| Externally published | Yes |
Abstract
A synthetic approach to recently reported and structurally unique 11(9→7)abeo-steroids pleurocin A/matsutakone (1) and pleurocin B (2) was developed by reconsidering the originally suggested polar transformations of their biogenesis. An intricate radical cyclization of a late stage intermediate followed by an oxidative quench was used instead and forged the abeo-framework, while the 9,11-seco-motif was obtained by conversion of ergosterol into a 9,11-secoenol ether employing a mercury-free desaturation of the Treibs type, an oxidative bond scission preluding a dioxa-[4+2]-cycloaddition of an aldehyde to an enone and a combined transacetalization/elimination followed by an ionic hydrogenation.
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemical Engineering(all)
- Colloid and Surface Chemistry
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In: Journal of the American Chemical Society, Vol. 141, No. 3, 23.01.2019, p. 1222-1226.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Translation of a Polar Biogenesis Proposal into a Radical Synthetic Approach: Synthesis of Pleurocin A/Matsutakone and Pleurocin B
AU - Heinze, Robert C.
AU - Heretsch, Philipp
N1 - Funding Information: Financial support for this work was provided by Deutsche Forschungsgemeinschaft (Grant HE 7133/5-1), the Boehringer Ingelheim Stiftung (exploration grant to P.H.), and Studienstiftung des deutschen Volkes (Ph.D. scholarship to R.C.H.). We are grateful to Alexander Ozimkovski for experimental assistance, to Fenja L. Duecker for assistance in preparing the manuscript, to Christiane Groneberg for HPLC separations, to Dr. Andreas Schafer̈ for NMR spectroscopic assistance, to Dr. Andreas Springer for mass spectrometric assistance, and to Prof. Dr. Dieter Lentz for X-ray crystallographic analyses (Freie Universitaẗ Berlin).
PY - 2019/1/23
Y1 - 2019/1/23
N2 - A synthetic approach to recently reported and structurally unique 11(9→7)abeo-steroids pleurocin A/matsutakone (1) and pleurocin B (2) was developed by reconsidering the originally suggested polar transformations of their biogenesis. An intricate radical cyclization of a late stage intermediate followed by an oxidative quench was used instead and forged the abeo-framework, while the 9,11-seco-motif was obtained by conversion of ergosterol into a 9,11-secoenol ether employing a mercury-free desaturation of the Treibs type, an oxidative bond scission preluding a dioxa-[4+2]-cycloaddition of an aldehyde to an enone and a combined transacetalization/elimination followed by an ionic hydrogenation.
AB - A synthetic approach to recently reported and structurally unique 11(9→7)abeo-steroids pleurocin A/matsutakone (1) and pleurocin B (2) was developed by reconsidering the originally suggested polar transformations of their biogenesis. An intricate radical cyclization of a late stage intermediate followed by an oxidative quench was used instead and forged the abeo-framework, while the 9,11-seco-motif was obtained by conversion of ergosterol into a 9,11-secoenol ether employing a mercury-free desaturation of the Treibs type, an oxidative bond scission preluding a dioxa-[4+2]-cycloaddition of an aldehyde to an enone and a combined transacetalization/elimination followed by an ionic hydrogenation.
UR - http://www.scopus.com/inward/record.url?scp=85060025191&partnerID=8YFLogxK
U2 - 10.1021/jacs.8b13356
DO - 10.1021/jacs.8b13356
M3 - Article
VL - 141
SP - 1222
EP - 1226
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 3
ER -