Abstract
Viriditoxin is a secondary metabolite isolated from Aspergillus viridinutans that has been shown to inhibit FtsZ, the bacterial homologue of eukaryotic tubulin. A streamlined, scalable, and highly diastereoselective synthesis of this complex natural product is described. Key advances include a more efficient synthesis of the requisite unsaturated pyranone, scalable assembly of the naphthopyranone monomer, and improved diastereoselectivity in the biaryl-coupling reaction. In addition, we disclose a serendipitous ruthenium-catalyzed anion dimerization resulting from trace metal left by an RCM reaction.
| Original language | English (US) |
|---|---|
| Article number | Z105311SS |
| Pages (from-to) | 362-371 |
| Number of pages | 10 |
| Journal | Synthesis |
| Volume | 44 |
| Issue number | 3 |
| DOIs | |
| State | Published - 2012 |
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Keywords
- antibiotics
- asymmetric synthesis
- atropisomerism
- biaryls
- natural products
ASJC Scopus subject areas
- Organic Chemistry
- Catalysis
Cite this
Second-generation synthesis of (-)-viriditoxin. / Grove, Charles I.; Fettinger, James C.; Shaw, Jared T.
In: Synthesis, Vol. 44, No. 3, Z105311SS, 2012, p. 362-371.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Second-generation synthesis of (-)-viriditoxin
AU - Grove, Charles I.
AU - Fettinger, James C.
AU - Shaw, Jared T.
PY - 2012
Y1 - 2012
N2 - Viriditoxin is a secondary metabolite isolated from Aspergillus viridinutans that has been shown to inhibit FtsZ, the bacterial homologue of eukaryotic tubulin. A streamlined, scalable, and highly diastereoselective synthesis of this complex natural product is described. Key advances include a more efficient synthesis of the requisite unsaturated pyranone, scalable assembly of the naphthopyranone monomer, and improved diastereoselectivity in the biaryl-coupling reaction. In addition, we disclose a serendipitous ruthenium-catalyzed anion dimerization resulting from trace metal left by an RCM reaction.
AB - Viriditoxin is a secondary metabolite isolated from Aspergillus viridinutans that has been shown to inhibit FtsZ, the bacterial homologue of eukaryotic tubulin. A streamlined, scalable, and highly diastereoselective synthesis of this complex natural product is described. Key advances include a more efficient synthesis of the requisite unsaturated pyranone, scalable assembly of the naphthopyranone monomer, and improved diastereoselectivity in the biaryl-coupling reaction. In addition, we disclose a serendipitous ruthenium-catalyzed anion dimerization resulting from trace metal left by an RCM reaction.
KW - antibiotics
KW - asymmetric synthesis
KW - atropisomerism
KW - biaryls
KW - natural products
UR - http://www.scopus.com/inward/record.url?scp=84856229465&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84856229465&partnerID=8YFLogxK
U2 - 10.1055/s-0031-1289651
DO - 10.1055/s-0031-1289651
M3 - Article
VL - 44
SP - 362
EP - 371
JO - Synthesis (Germany)
JF - Synthesis (Germany)
SN - 0039-7881
IS - 3
M1 - Z105311SS
ER -