The first synthetic studies on pestalotiopsin A. A stereocontrolled approach to the functionalised bicyclic core
Literature Information
Derek Johnston, Emmanuel Couché, David J. Edmonds, Kenneth W. Muir, David J. Procter
Pestalotiopsin A is a structurally unique, caryophyllene-type sesquiterpene which has shown immunosuppressive activity and cytotoxicity in preliminary assays. A stereocontrolled approach to the functionalised 2-oxabicyclo[3.2.0]heptane core of pestalotiopsin A is described. This constitutes the first synthetic studies on pestalotiopsin A. Our approach includes a samarium(II)-mediated 4-exo-trig cyclisation and a trans-lactonisation process triggered by the addition of alkylytterbium reagents to a cyclobutanone intermediate. Further manipulation provides access to advanced intermediates which are excellent precursors for the future construction of the final ring of the target.
Recommended Journals
Related Literature
Mutual induced coordination in halogen-bonded anionic assemblies with (6,3) cation-templated topologies
Pierangelo Metrangolo, Frank Meyer, Tullio Pilati, Giancarlo Terraneo
DOI: 10.1039/B716879A
Cu-catalyzed stereoselective conjugate addition of arylboronic acids to alkynoates
Yoshihiko Yamamoto, Naohiro Kirai, Yu Harada
DOI: 10.1039/B802231C
Use of ionic liquids (ILs) for the IL-anion size-dependent formation of Cr, Mo and W nanoparticles from metal carbonyl M(CO)6 precursors
Engelbert Redel, Ralf Thomann, Christoph Janiak
DOI: 10.1039/B718055A
Accelerating charge transfer in a triphenylamine–subphthalocyanine donor–acceptor system
Anaïs Medina, Christian G. Claessens, G. M. Aminur Rahman, Al Mokhtar Lamsabhi, Otilia Mó, Manuel Yáñez, Dirk M. Guldi, Tomás Torres
DOI: 10.1039/B719226F
Functionalized polyesters from organocatalyzed ROP of gluOCA, the O-carboxyanhydride derived from glutamic acid
Olivier Thillaye du Boullay, Colin Bonduelle, Blanca Martin-Vaca, Didier Bourissou
DOI: 10.1039/B800852C
A unique heterobimetallic benzyl calciate—an organometallic mixed-metal species involving a heavy alkaline-earth metal
Marites A. Guino-o, Charles F. Campana, Karin Ruhlandt-Senge
DOI: 10.1039/B715701K
Rapid formation of metal–organic nano-capsules gives new insight into the self-assembly process‡
Nicholas P. Power, John E. Warren, Jerry L. Atwood
DOI: 10.1039/B719769A
You might also like
What is the market or research trend for N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0)?
N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0) is increasingly being used ...
What precautions should be taken when handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate (CAS: 1050507-06-6)?
When handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate, appropriate p...
What regulatory guidelines apply to diethyldiselane (CAS: 628-39-7)?
Diethyldiselane (CAS: 628-39-7) is classified under the Globally Harmonized Syst...
What is the market or research trend for oxocopper (CAS: 12053-18-8)?
The market for oxocopper (CAS: 12053-18-8) is primarily driven by its use in cat...
What is the market or research trend for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-carboxylic acid?
The market for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-c...
What is 2-(1-Pyrrolidinyl)-4-pyridinamine (CAS: 35981-63-6)?
2-(1-Pyrrolidinyl)-4-pyridinamine is a chemical compound with the CAS number 359...
What are the physical and chemical properties of 2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1)?
2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1) is a crystalline sol...
How is (S)-Alpha-allyl-proline hydrochloride (CAS: 129704-91-2) typically synthesized?
(S)-Alpha-allyl-proline hydrochloride is usually synthesized via a Wittig reacti...
What is 3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5)?
3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5) is an organic compound w...
How is Lys-SMCC-DM1 (CAS: 1281816-04-3) typically synthesized?
Lys-SMCC-DM1 is synthesized via a multi-step process involving the coupling of S...
Source Journal
Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.











![N-{15-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl}-2-(2-propyn-1-yloxy)acetamide structure N-{15-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl}-2-(2-propyn-1-yloxy)acetamide structure](https://static.chemtradehub.com/structs/210/2101206-92-0-2eb5.webp)


