Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 2320-2322 |
| Seitenumfang | 3 |
| Fachzeitschrift | Organic letters |
| Jahrgang | 18 |
| Ausgabenummer | 9 |
| Frühes Online-Datum | 22 Apr. 2016 |
| Publikationsstatus | Veröffentlicht - 6 Mai 2016 |
Abstract
The synthesis of (+)-omphadiol and (+)-pyxidatol C was achieved through two independent strategies. For the synthesis of (+)-omphadiol, dicyclopentadienone was used as the workbench on which the three contiguous stereocenters of the cyclopentane could be introduced selectively. These include a tertiary alcohol and a selective protonation of an enolate. A ring-closing metathesis and a cyclopropanation concluded the synthesis. For the synthesis of pyxidatol C, we used the epoxide derived from (R)-linalool that was transformed to cyclopentane 23. After chain extension, another ring-closing metathesis followed by oxidation state changes and finally a cyclopropanation led to (+)-pyxidatol C.
ASJC Scopus Sachgebiete
- Biochemie, Genetik und Molekularbiologie (insg.)
- Biochemie
- Chemie (insg.)
- Physikalische und Theoretische Chemie
- Chemie (insg.)
- Organische Chemie
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in: Organic letters, Jahrgang 18, Nr. 9, 06.05.2016, S. 2320-2322.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Synthesis of (+)-Omphadiol and (+)-Pyxidatol C
AU - Parthasarathy, Gowrisankar
AU - Eggert, Ulrike
AU - Kalesse, Markus
N1 - The analytics team at the Institute of Organic Chemistry and Dr. M. Wiebcke (for X-ray analysis) are gratefully acknowledged for their support.
PY - 2016/5/6
Y1 - 2016/5/6
N2 - The synthesis of (+)-omphadiol and (+)-pyxidatol C was achieved through two independent strategies. For the synthesis of (+)-omphadiol, dicyclopentadienone was used as the workbench on which the three contiguous stereocenters of the cyclopentane could be introduced selectively. These include a tertiary alcohol and a selective protonation of an enolate. A ring-closing metathesis and a cyclopropanation concluded the synthesis. For the synthesis of pyxidatol C, we used the epoxide derived from (R)-linalool that was transformed to cyclopentane 23. After chain extension, another ring-closing metathesis followed by oxidation state changes and finally a cyclopropanation led to (+)-pyxidatol C.
AB - The synthesis of (+)-omphadiol and (+)-pyxidatol C was achieved through two independent strategies. For the synthesis of (+)-omphadiol, dicyclopentadienone was used as the workbench on which the three contiguous stereocenters of the cyclopentane could be introduced selectively. These include a tertiary alcohol and a selective protonation of an enolate. A ring-closing metathesis and a cyclopropanation concluded the synthesis. For the synthesis of pyxidatol C, we used the epoxide derived from (R)-linalool that was transformed to cyclopentane 23. After chain extension, another ring-closing metathesis followed by oxidation state changes and finally a cyclopropanation led to (+)-pyxidatol C.
UR - http://www.scopus.com/inward/record.url?scp=84969685296&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.6b00814
DO - 10.1021/acs.orglett.6b00814
M3 - Article
AN - SCOPUS:84969685296
VL - 18
SP - 2320
EP - 2322
JO - Organic letters
JF - Organic letters
SN - 1523-7060
IS - 9
ER -