Concepedia

Total Synthesis of Salinosporamide A

Takeo Fukuda, Kouhei Sugiyama, Shiho Arima, Yoshihiro Harigaya, Tohru Nagamitsu, Satoshi Ōmura

Organic Letters · 2008 · 53 citations · 17 references

DOI

Concepts

Abstract

The total synthesis of salinosporamide A has been achieved through enzymatic desymmetrization, diastereoselective aldol reaction, intramolecular aldol reaction, and intermolecular Reformatsky-type reaction followed by 1,4-reduction as key reactions.

References

17

Salinosporamide A: A Highly Cytotoxic Proteasome Inhibitor from a Novel Microbial Source, a Marine Bacterium of the New Genus <i>Salinospora</i>

Robert H. Feling, Greg O. Buchanan, Tracy J. Mincer et al. · Angewandte Chemie International Edition · 2003 · 1.1K citations · Full text

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A novel orally active proteasome inhibitor induces apoptosis in multiple myeloma cells with mechanisms distinct from Bortezomib

Dharminder Chauhan, Laurence Catley, Guilan Li et al. · Cancer Cell · 2005 · 698 citations · Full text

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A Simple Stereocontrolled Synthesis of Salinosporamide A

Leleti Rajender Reddy, P. Saravanan, E. J. Corey · Journal of the American Chemical Society · 2004 · 245 citations

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Structure−Activity Relationship Studies of Salinosporamide A (NPI-0052), a Novel Marine Derived Proteasome Inhibitor

Venkat R. Macherla, Scott S. Mitchell, Rama Rao Manam et al. · Journal of Medicinal Chemistry · 2005 · 235 citations

, , +15

Total Synthesis and Biological Activity of Lactacystin, Omuralide and Analogs.

E. J. Corey, Wei‐Dong Z. Li · Chemical and Pharmaceutical Bulletin · 1999 · 190 citations · Full text

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