Details
| Original language | German |
|---|---|
| Pages (from-to) | 933-936 |
| Number of pages | 4 |
| Journal | Liebigs Annalen der Chemie |
| Volume | 1991 |
| Issue number | 9 |
| Publication status | Published - 12 Sept 1991 |
| Externally published | Yes |
Abstract
Synthesis of rac‐Norartemeseol The synthesis of the terpenoid rac‐norartemesol (1b) is accomplished using epoxide ring‐opening reactions as key steps. Thus, addition of the thio‐substituted allyl anion 2b to ethylene oxide followed by proton‐induced cyclisation provides the tetrahydrofuran 4a. The oxirane 6, which is formed by simple functional group interconversion, is opened by the diethylaluminium salt 10 of a propargylsilane. After catalytic hydrogenation and tosylation, fluoride‐induced cyclisation of the allylsilane 13 gives the target molecule 1b.
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Liebigs Annalen der Chemie, Vol. 1991, No. 9, 12.09.1991, p. 933-936.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthese von rac‐Norartemeseol
AU - Kirschning, Andreas
AU - Narjes, Frank
AU - Schaumann, Ernst
PY - 1991/9/12
Y1 - 1991/9/12
N2 - Synthesis of rac‐Norartemeseol The synthesis of the terpenoid rac‐norartemesol (1b) is accomplished using epoxide ring‐opening reactions as key steps. Thus, addition of the thio‐substituted allyl anion 2b to ethylene oxide followed by proton‐induced cyclisation provides the tetrahydrofuran 4a. The oxirane 6, which is formed by simple functional group interconversion, is opened by the diethylaluminium salt 10 of a propargylsilane. After catalytic hydrogenation and tosylation, fluoride‐induced cyclisation of the allylsilane 13 gives the target molecule 1b.
AB - Synthesis of rac‐Norartemeseol The synthesis of the terpenoid rac‐norartemesol (1b) is accomplished using epoxide ring‐opening reactions as key steps. Thus, addition of the thio‐substituted allyl anion 2b to ethylene oxide followed by proton‐induced cyclisation provides the tetrahydrofuran 4a. The oxirane 6, which is formed by simple functional group interconversion, is opened by the diethylaluminium salt 10 of a propargylsilane. After catalytic hydrogenation and tosylation, fluoride‐induced cyclisation of the allylsilane 13 gives the target molecule 1b.
KW - Allyl anion, hetero‐substituted
KW - Cyclopropane, vinyl‐
KW - Norartemeseol, rac‐
KW - Oxiranes, ring‐opening
KW - Tetrahydrofuran, substituted
UR - http://www.scopus.com/inward/record.url?scp=84986641959&partnerID=8YFLogxK
U2 - 10.1002/jlac.1991199101159
DO - 10.1002/jlac.1991199101159
M3 - Artikel
AN - SCOPUS:84986641959
VL - 1991
SP - 933
EP - 936
JO - Liebigs Annalen der Chemie
JF - Liebigs Annalen der Chemie
SN - 0170-2041
IS - 9
ER -