Total synthesis of FR901464, an antitumor agent that regulates the transcription of oncogenes and tumor suppressor genes

Journal of the American Chemical Society
Brian J AlbertKazunori Koide

Abstract

FR901464 is a potent anticancer agent that regulates the transcription of oncogenes and tumor suppressor genes. A convergent enantioselective synthesis of FR901464 was accomplished in 13 linear steps. Central to the synthetic approach was the diene-ene cross olefin metathesis reaction to generate the C6-C7 olefin, without the use of protecting groups, as the final coupling. Additional key reactions include a Zr/Ag-promoted alkynylation to set the C4 stereocenter, a mild and chemoselective Red-Al reduction, a stereoselective Mislow-Evans-type [2,3]-sigmatropic rearrangement to install the C5 stereocenter, a Carreira asymmetric alkynylation to generate the C4' stereocenter, and a highly efficient ring-closing metathesis-allylic oxidation sequence to form an unsaturated lactone.

References

Oct 11, 2001·Journal of the American Chemical Society·C F ThompsonE N Jacobsen
Nov 2, 2002·Angewandte Chemie·Karol GrelaAnna Michrowska
May 6, 2004·Angewandte Chemie·Shatrughan P Shahi, Kazunori Koide
Oct 8, 2004·Organic Letters·Brian J Albert, Kazunori Koide

❮ Previous
Next ❯

Citations

Dec 12, 2013·Journal of Medicinal Chemistry·Chandraiah LagisettiThomas R Webb
Nov 3, 2009·Journal of Medicinal Chemistry·Chandraiah LagisettiThomas R Webb
Jun 9, 2016·Journal of the American Chemical Society·K C NicolaouS Mothish Kumar
Oct 26, 2012·Chemistry : a European Journal·Barry M TrostVincent S Chan
Jun 24, 2006·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Karol GrelaMichał Bieniek
Oct 2, 2007·Chembiochem : a European Journal of Chemical Biology·Brian J Albert, Kazunori Koide
Dec 29, 2007·Chembiochem : a European Journal of Chemical Biology·Kazunori KoideNeil A Hukriede
Jan 16, 2009·Angewandte Chemie·David TejedorFernando García-Tellado
Feb 17, 2009·Chemistry : a European Journal·Jiang-Chun ZhongMin Wang
May 1, 2009·Advanced Synthesis & Catalysis·Barry M Trost, Andrew H Weiss
Feb 22, 2012·Organic & Biomolecular Chemistry·Pipas SahaAnil K Saikia
Jul 22, 2016·Wiley Interdisciplinary Reviews. RNA·Kerstin A EffenbergerMelissa S Jurica
Aug 25, 2020·Beilstein Journal of Organic Chemistry·William A Donaldson
Jan 13, 2011·Chemistry : a European Journal·Sami OsmanKazunori Koide
Nov 16, 2007·Organic Letters·Amanda L Garner, Kazunori Koide
Aug 5, 2021·The Journal of Antibiotics·Tilman Schneider-PoetschMinoru Yoshida
Apr 27, 2018·The Journal of Organic Chemistry·Arun K GhoshMelissa S Jurica
Oct 20, 2020·Organic Letters·Christopher GartshoreDale L Boger
Nov 26, 2014·Organic Letters·Arun K GhoshMelissa S Jurica
Mar 13, 2020·The Journal of Organic Chemistry·Robert K BressinKazunori Koide

❮ 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.