A Modular Formal Total Synthesis of (±)-Cycloclavine

The Journal of Organic Chemistry
Natalie Netz, Till Opatz

Abstract

Cycloclavine is a clavine-type Ergot alkaloid noteworthy for its unique pentacyclic skeleton featuring a 3-azabicyclo[3.1.0]hexane substructure. A short convergent route to the racemic alkaloid is described which comprises only eight linear steps and requires only four chromatographic purifications. The two key building blocks can be prepared in high yield from commercially available starting materials. Two consecutive coupling reactions, namely a selective alkylation of a dienolate and a Heck reaction, are the key steps of the reaction sequence.

References

Feb 15, 1984·Biochemical Pharmacology·E EichW E Müller
Oct 24, 2001·The Journal of Organic Chemistry·Hugo E. GottliebAbraham Nudelman
Aug 27, 2005·The Journal of Organic Chemistry·James R DaviesChristopher J Moody
Feb 22, 2008·Bioorganic & Medicinal Chemistry·Kumiko SakoMasanori Baba
Jul 12, 2008·Pharmazie in unserer Zeit·Andrea Sinz
Jul 18, 2009·Journal of the American Chemical Society·Michael E MuratoreDarren J Dixon
Apr 27, 2011·Journal of the American Chemical Society·Filip R Petronijevic, Peter Wipf
Nov 28, 2013·The Journal of Organic Chemistry·Wei WangXiao-Ping Cao
Feb 11, 2014·Tetrahedron Letters·Nitinkumar D JabreMatthias Brewer
Oct 7, 2014·Organic & Biomolecular Chemistry·Dadong LiJames W Canary

❮ Previous
Next ❯

Citations

May 26, 2017·The Journal of Organic Chemistry·Ramarao Parella, Srinivasarao Arulananda Babu
Nov 20, 2016·Angewandte Chemie·Stephanie R McCabe, Peter Wipf
May 10, 2018·Organic & Biomolecular Chemistry·Jin-Quan ChenXiao-Ping Cao
May 25, 2016·Organic & Biomolecular Chemistry·Stephanie R McCabe, Peter Wipf
Nov 8, 2017·Chemical Communications : Chem Comm·Jin-Quan ChenXiao-Ping Cao
Jan 11, 2018·Chemical Communications : Chem Comm·Saikat ChaudhuriAlakesh Bisai
Jul 7, 2018·Journal of the American Chemical Society·Lin DengGuangbin Dong

❮ 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.