Abstract
(matrix presented) epi-7-Deoxypancratistatin containing the cis-fused phenanthridone core was synthesized in 12 steps from bromobenzene. Key features of this synthesis include the enzymatic oxidation of bromobenzene with toluene dioxygenase, selective opening of a cyclic sulfate over an aziridine with oxygen nucleophiles, and an intramolecular Lewis acid-catalyzed cyclization onto an epoxy conduramine derived via aza-Payne rearrangement.
| Original language | English |
|---|---|
| Pages (from-to) | 115-117 |
| Number of pages | 3 |
| Journal | Organic Letters |
| Volume | 4 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - Jan 10 2002 |
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ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
Total synthesis of epi-7-deoxypancratistatin via aza-payne rearrangement and intramolecular cyclization. / Rinner, Uwe; Siengalewicz, Peter; Hudlicky, Tomas.
In: Organic Letters, Vol. 4, No. 1, 10.01.2002, p. 115-117.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Total synthesis of epi-7-deoxypancratistatin via aza-payne rearrangement and intramolecular cyclization
AU - Rinner, Uwe
AU - Siengalewicz, Peter
AU - Hudlicky, Tomas
PY - 2002/1/10
Y1 - 2002/1/10
N2 - (matrix presented) epi-7-Deoxypancratistatin containing the cis-fused phenanthridone core was synthesized in 12 steps from bromobenzene. Key features of this synthesis include the enzymatic oxidation of bromobenzene with toluene dioxygenase, selective opening of a cyclic sulfate over an aziridine with oxygen nucleophiles, and an intramolecular Lewis acid-catalyzed cyclization onto an epoxy conduramine derived via aza-Payne rearrangement.
AB - (matrix presented) epi-7-Deoxypancratistatin containing the cis-fused phenanthridone core was synthesized in 12 steps from bromobenzene. Key features of this synthesis include the enzymatic oxidation of bromobenzene with toluene dioxygenase, selective opening of a cyclic sulfate over an aziridine with oxygen nucleophiles, and an intramolecular Lewis acid-catalyzed cyclization onto an epoxy conduramine derived via aza-Payne rearrangement.
UR - http://www.scopus.com/inward/record.url?scp=0037050522&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0037050522&partnerID=8YFLogxK
U2 - 10.1021/ol0169877
DO - 10.1021/ol0169877
M3 - Article
C2 - 11772104
AN - SCOPUS:0037050522
VL - 4
SP - 115
EP - 117
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 1
ER -