Issue 16, 2007
From the journal:

Organic & Biomolecular Chemistry

Model studies toward the synthesis of the bioactive diterpenoid, harringtonolide†

Timothy P. O'Sullivan,*a   Hongbin Zhangb  and  Lewis N. Manderc  

* Corresponding authors

a Department of Chemistry, University College Cork, Cork, Ireland
E-mail: tim.osullivan@ucc.ie
Fax: +353 21 490 1656
Tel: +353 21 490 1655

b Key Laboratory of Medicinal Chemistry for Natural Resources, Yunnan University, Kunming, P. R. C
E-mail: zhanghb@ynu.edu.cn
Fax: +86 871 5035538
Tel: +86 871 5031119

c Research School of Chemistry, Australian National University, Canberra, Australia
E-mail: mander@rsc.anu.edu.au
Fax: +61 2 6125 0750
Tel: +61 2 6125 3761

Abstract

In model studies towards the synthesis of harringtonolide, the construction of the tropone moiety viaarene cyclopropanation was investigated. The installation of the lactone ring was accomplished by way of a Diels–Alder cycloaddition of various indenones and α-pyones. The incorporation of the key bridge methyl group and subsequent control of its stereochemistry is also outlined.

Graphical abstract: Model studies toward the synthesis of the bioactive diterpenoid, harringtonolide

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Article information

DOI
https://doi.org/10.1039/B707467K
Article type
Paper
Submitted
17 May 2007
Accepted
19 Jun 2007
First published
02 Jul 2007

Org. Biomol. Chem., 2007,5, 2627-2635

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Model studies toward the synthesis of the bioactive diterpenoid, harringtonolide

T. P. O'Sullivan, H. Zhang and L. N. Mander, Org. Biomol. Chem., 2007, 5, 2627 DOI: 10.1039/B707467K

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