Details
| Original language | English |
|---|---|
| Pages (from-to) | 1129-1136 |
| Number of pages | 8 |
| Journal | Chemistry - a European journal |
| Volume | 9 |
| Issue number | 5 |
| Publication status | Published - 21 Feb 2003 |
Abstract
Callystatin A is a prominent member of a class of natural products which display promising growth inhibition of cancer cells in their biological profile. The challenging structure and the interesting biological activity of (-)callystatin A fueled our interest in the synthesis of this marine natural product. We achieved the total synthesis using a highly convergent approach joining four subunits together with a Wittig olefination, a selective Heck reaction and an aldol reaction as the pivotal steps. The aldol reaction as one of the final transformations during the synthesis opens fast access to a variety of structural analogues and circumvents tedious protecting group manipulations. Here we report an improved synthesis utilizing a modified vinyl iodide which shortens the synthesis by two steps. Additionally, first biological results will be reported.
Keywords
- Aldol reaction, Antibiotics, Callystatin, Heck reaction, Polyketides
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
Sustainable Development Goals
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In: Chemistry - a European journal, Vol. 9, No. 5, 21.02.2003, p. 1129-1136.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - The Total Synthesis of (-)-Callystatin A
AU - Kalesse, Markus
AU - Chary, Khandavalli P.
AU - Quitschalle, Monika
AU - Burzlaff, Arne
AU - Kasper, Cornelia
AU - Scheper, Thomas
PY - 2003/2/21
Y1 - 2003/2/21
N2 - Callystatin A is a prominent member of a class of natural products which display promising growth inhibition of cancer cells in their biological profile. The challenging structure and the interesting biological activity of (-)callystatin A fueled our interest in the synthesis of this marine natural product. We achieved the total synthesis using a highly convergent approach joining four subunits together with a Wittig olefination, a selective Heck reaction and an aldol reaction as the pivotal steps. The aldol reaction as one of the final transformations during the synthesis opens fast access to a variety of structural analogues and circumvents tedious protecting group manipulations. Here we report an improved synthesis utilizing a modified vinyl iodide which shortens the synthesis by two steps. Additionally, first biological results will be reported.
AB - Callystatin A is a prominent member of a class of natural products which display promising growth inhibition of cancer cells in their biological profile. The challenging structure and the interesting biological activity of (-)callystatin A fueled our interest in the synthesis of this marine natural product. We achieved the total synthesis using a highly convergent approach joining four subunits together with a Wittig olefination, a selective Heck reaction and an aldol reaction as the pivotal steps. The aldol reaction as one of the final transformations during the synthesis opens fast access to a variety of structural analogues and circumvents tedious protecting group manipulations. Here we report an improved synthesis utilizing a modified vinyl iodide which shortens the synthesis by two steps. Additionally, first biological results will be reported.
KW - Aldol reaction
KW - Antibiotics
KW - Callystatin
KW - Heck reaction
KW - Polyketides
UR - http://www.scopus.com/inward/record.url?scp=0037416694&partnerID=8YFLogxK
U2 - 10.1002/chem.200390130
DO - 10.1002/chem.200390130
M3 - Article
C2 - 12596149
AN - SCOPUS:0037416694
VL - 9
SP - 1129
EP - 1136
JO - Chemistry - a European journal
JF - Chemistry - a European journal
SN - 0947-6539
IS - 5
ER -