Details
| Original language | English |
|---|---|
| Pages (from-to) | 998-1001 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 21 |
| Issue number | 4 |
| Early online date | 29 Jan 2019 |
| Publication status | Published - 15 Feb 2019 |
Abstract
A biomimetic, regio- and stereoselective approach to the 5,6,11-tricyclic core skeleton of xenovulene A, as well as sterhirsutins A and B, is described. The key steps are a biomimetic inverse-electron-demand hetero-Diels-Alder cycloaddition of α-humulene and a ribose-derived vinyl ketone, followed by acid-catalyzed rearrangement of the 1,3-dioxolane that neighbors the resultant cyclic enol ether.
Keywords
- Biomimetic Materials/chemistry, Cycloaddition Reaction, Models, Molecular, Molecular Conformation, Sesquiterpenes/chemical synthesis
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic Letters, Vol. 21, No. 4, 15.02.2019, p. 998-1001.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - A General Biomimetic Hetero-Diels-Alder Approach to the Core Skeletons of Xenovulene A and the Sterhirsutins A and B
AU - Li, Pei-Jun
AU - Dräger, Gerald
AU - Kirschning, Andreas
N1 - Funding information: Finally, acid-catalyzed rearrangement of acetonides 18a and 18b provided enones 20a and 20b, respectively (Scheme 3). This transformation was not initially expected, but to our delight, it provided a desirable advanced intermediate in one step, which is poised for late-stage modification to the full structure of xenovulene A (1) and sterhirsutene A (2). A plausible mechanism for this unique transformation is summarized in Scheme 5. Supported by the oxygen atom P.-J.L. is thankful to the Hannover School of Biomolecular Drug Research (HSBDR) doctoral training center for financial support. Helpful discussions from Dr. Michael Wolling (Boehringer Ingelheim AG & Co. KG, Germany) and Dr. Matthew D. Norris (Leibniz Universita?t Hannover) are kindly acknowledged.
PY - 2019/2/15
Y1 - 2019/2/15
N2 - A biomimetic, regio- and stereoselective approach to the 5,6,11-tricyclic core skeleton of xenovulene A, as well as sterhirsutins A and B, is described. The key steps are a biomimetic inverse-electron-demand hetero-Diels-Alder cycloaddition of α-humulene and a ribose-derived vinyl ketone, followed by acid-catalyzed rearrangement of the 1,3-dioxolane that neighbors the resultant cyclic enol ether.
AB - A biomimetic, regio- and stereoselective approach to the 5,6,11-tricyclic core skeleton of xenovulene A, as well as sterhirsutins A and B, is described. The key steps are a biomimetic inverse-electron-demand hetero-Diels-Alder cycloaddition of α-humulene and a ribose-derived vinyl ketone, followed by acid-catalyzed rearrangement of the 1,3-dioxolane that neighbors the resultant cyclic enol ether.
KW - Biomimetic Materials/chemistry
KW - Cycloaddition Reaction
KW - Models, Molecular
KW - Molecular Conformation
KW - Sesquiterpenes/chemical synthesis
UR - http://www.scopus.com/inward/record.url?scp=85061268586&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.8b04003
DO - 10.1021/acs.orglett.8b04003
M3 - Article
C2 - 30694066
AN - SCOPUS:85061268586
VL - 21
SP - 998
EP - 1001
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 4
ER -