Abstract
Synthesis of the indenotryptoline bisindole alkaloid, BE-54017, was accomplished using osmium-promoted cis-dihydroxylation of maleimide as a key step. After optical resolution, the absolute configuration of this molecule was determined by comparing its optical rotation and HPLC profile to those obtained for BE-54017 derived from enantiopure cladoniamide A, whose stereochemistry has been reported previously. BE-54017 with the correct absolute stereochemistry induced apoptosis of epidermal growth factor (EGF)-stimulated EGF receptor overexpressing A431 cells and inhibited vacuolar-type H+-ATPase (V-ATPase).
| Original language | English |
|---|---|
| Pages (from-to) | 4418-4421 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 14 |
| Issue number | 17 |
| DOIs | |
| Publication status | Published - 2012 Sep 7 |
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ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
- Biochemistry
Cite this
Synthesis and assignment of the absolute configuration of indenotryptoline bisindole alkaloid BE-54017. / Kimura, Tomoyuki; Kanagaki, Shuhei; Matsui, Yusuke; Imoto, Masaya; Watanabe, Takumi; Shibasaki, Masakatsu.
In: Organic Letters, Vol. 14, No. 17, 07.09.2012, p. 4418-4421.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis and assignment of the absolute configuration of indenotryptoline bisindole alkaloid BE-54017
AU - Kimura, Tomoyuki
AU - Kanagaki, Shuhei
AU - Matsui, Yusuke
AU - Imoto, Masaya
AU - Watanabe, Takumi
AU - Shibasaki, Masakatsu
PY - 2012/9/7
Y1 - 2012/9/7
N2 - Synthesis of the indenotryptoline bisindole alkaloid, BE-54017, was accomplished using osmium-promoted cis-dihydroxylation of maleimide as a key step. After optical resolution, the absolute configuration of this molecule was determined by comparing its optical rotation and HPLC profile to those obtained for BE-54017 derived from enantiopure cladoniamide A, whose stereochemistry has been reported previously. BE-54017 with the correct absolute stereochemistry induced apoptosis of epidermal growth factor (EGF)-stimulated EGF receptor overexpressing A431 cells and inhibited vacuolar-type H+-ATPase (V-ATPase).
AB - Synthesis of the indenotryptoline bisindole alkaloid, BE-54017, was accomplished using osmium-promoted cis-dihydroxylation of maleimide as a key step. After optical resolution, the absolute configuration of this molecule was determined by comparing its optical rotation and HPLC profile to those obtained for BE-54017 derived from enantiopure cladoniamide A, whose stereochemistry has been reported previously. BE-54017 with the correct absolute stereochemistry induced apoptosis of epidermal growth factor (EGF)-stimulated EGF receptor overexpressing A431 cells and inhibited vacuolar-type H+-ATPase (V-ATPase).
UR - http://www.scopus.com/inward/record.url?scp=84866050030&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84866050030&partnerID=8YFLogxK
U2 - 10.1021/ol3019314
DO - 10.1021/ol3019314
M3 - Article
C2 - 22917065
AN - SCOPUS:84866050030
VL - 14
SP - 4418
EP - 4421
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 17
ER -