Details
| Original language | English |
|---|---|
| Pages (from-to) | 2320-2322 |
| Number of pages | 3 |
| Journal | Organic letters |
| Volume | 18 |
| Issue number | 9 |
| Early online date | 22 Apr 2016 |
| Publication status | Published - 6 May 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 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. 18, No. 9, 06.05.2016, p. 2320-2322.
Research output: Contribution to journal › Article › Research › 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 -