An aldol approach to the total synthesis of pamamycin 621 A

Organic Letters
Guo-Bao Ren, Yikang Wu

Abstract

Pamamycin 621A was synthesized through a convergent route, with the THF rings constructed from Evans aldols in the presence of the chiral auxiliaries without suffering racemization or elimination. The basic amino group was introduced at a late stage through reduction of an azido group with n-Bu(3)SnH, which also demonstrates for the first time the great potential of this largely forgotten reduction protocol in synthesis of multifunctional substrates.

References

Jul 1, 1979·The Journal of Antibiotics·P A McCann, B M Pogell
Oct 1, 1995·The Journal of Antibiotics·M NatsumeS Marumo
Oct 11, 2001·Journal of the American Chemical Society·E LeeS K Hong
Jan 17, 2002·Journal of the American Chemical Society·David A EvansC Wade Downey
Apr 2, 2002·Organic Letters·David A EvansJason S Tedrow
Dec 6, 2002·Journal of the American Chemical Society·Eun Jeong JeongEun Lee
Mar 12, 2005·The Journal of Organic Chemistry·P Veeraraghavan RamachandranM Venkat Ram Reddy
Nov 5, 2005·Organic Letters·James A MarshallAndrew Nolting
Jun 16, 2006·Organic Letters·Yikang Wu, Ya-Ping Sun
Apr 15, 2002·Angewandte Chemie·Sung Ho KangSung Bae Lee

❮ Previous
Next ❯

Citations

Apr 12, 2012·Angewandte Chemie·Yang Zou, Yikang Wu
Jan 31, 2019·Journal of Physics. Condensed Matter : an Institute of Physics Journal·Francisco ColmeneroVicente Timón
Feb 9, 2019·Journal of Physics. Condensed Matter : an Institute of Physics Journal·Chao LiuWei Ren
Oct 21, 2011·Chemistry : a European Journal·Petra FischerPeter Metz
Dec 30, 2014·Angewandte Chemie·Yuriy RebetsAndriy Luzhetskyy
Jul 6, 2010·The Journal of Organic Chemistry·Guo-Bao RenYikang Wu

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.