Details
| Original language | English |
|---|---|
| Pages (from-to) | 3889-3892 |
| Number of pages | 4 |
| Journal | Organic letters |
| Volume | 6 |
| Issue number | 22 |
| Publication status | Published - 28 Oct 2004 |
Abstract
(Chemical Equation Presented) The synthesis of the A,B,C-ring system (2) of hexacyclinic acid (1) is achieved starting from a selective Diels-Alder reaction followed by vinyl cuprate addition. The diastereoselective reduction of the ketone carbonyl at C16 could be achieved with LiAlH4. An intramolecular Michael addition established the ring system stereoselectively, providing access to the selective generation of 9 out of the 14 stereocenters of hexacyclinic acid.
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. 6, No. 22, 28.10.2004, p. 3889-3892.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthesis of the A,B,C-ring system of hexacyclinic acid
AU - Stellfeld, Timo
AU - Bhatt, Ulhas
AU - Kalesse, Markus
PY - 2004/10/28
Y1 - 2004/10/28
N2 - (Chemical Equation Presented) The synthesis of the A,B,C-ring system (2) of hexacyclinic acid (1) is achieved starting from a selective Diels-Alder reaction followed by vinyl cuprate addition. The diastereoselective reduction of the ketone carbonyl at C16 could be achieved with LiAlH4. An intramolecular Michael addition established the ring system stereoselectively, providing access to the selective generation of 9 out of the 14 stereocenters of hexacyclinic acid.
AB - (Chemical Equation Presented) The synthesis of the A,B,C-ring system (2) of hexacyclinic acid (1) is achieved starting from a selective Diels-Alder reaction followed by vinyl cuprate addition. The diastereoselective reduction of the ketone carbonyl at C16 could be achieved with LiAlH4. An intramolecular Michael addition established the ring system stereoselectively, providing access to the selective generation of 9 out of the 14 stereocenters of hexacyclinic acid.
UR - http://www.scopus.com/inward/record.url?scp=8744279021&partnerID=8YFLogxK
U2 - 10.1021/ol048720o
DO - 10.1021/ol048720o
M3 - Article
C2 - 15496056
AN - SCOPUS:8744279021
VL - 6
SP - 3889
EP - 3892
JO - Organic letters
JF - Organic letters
SN - 1523-7060
IS - 22
ER -