Rapid synthesis of the [5-5-6-6] tetracyclic system in the spirobionaphthalene natural product spiropreussione B was achieved. An intramolecular, thermal dehydrogenative Diels–Alder reaction was employed as the key step. Furthermore, this approach was extended to generate a library of structurally novel linear tetracyclic systems of spiropreussione B in a highly efficient manner. This report constitutes the first synthetic approach to the spiropreussione B natural product. © 2017 WILEY-VCH Verlag GmbH &amp; Co. KGaA, Weinheim

Beeraiah Baire

Department Of Chemistry

Bhavani Shankar Chinta

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

European Journal of Organic Chemistry

First Synthesis of the [5-5-6-6] Tetracyclic Framework of Spiropreussione B

An efficient and convenient synthesis of advanced (highly functionalized) tricyclic frame works present in the isofuranonaphthalenone, nodulones A-C and xestolactone A natural products has been achieved. The dehydro Diels-Alder reaction was employed as the key step for the construction of tricyclic systems. © 2016 Elsevier Ltd

Tetrahedron

The dehydro Diels-Alder (DDA) reaction based approach to isofuranonaphthalenone, nodulones A-C and xestolactone A

A mild, cascade methodology based on the modified Cadiot-Chodkiewicz reaction was developed for the stereoselective synthesis of trans-enynones. By this methodology, structurally divergent trans-enynones, which are embedded with sensitive functional groups, were synthesized. Control experiments suggested that the CuCl alone does not have a role in the isomerization step, whereas the CuCl-piperidine complex (formed during the cross coupling) may have a rate enhancing effect. Furthermore, additional sets of control experiments favor the involvement of unimolecular [1,2]-H shift rather than a homobimolecular proton abstraction during the isomerization step. © 2015 American Chemical Society.

Journal	Data powered by TypesetEuropean Journal of Organic Chemistry
Publisher	Data powered by TypesetWiley-VCH Verlag
ISSN	1434193X
Open Access	No