Issue 3, 2004

A two-directional synthesis of the C58C71 fragment of palytoxin

Abstract

A two directional approach, in which asymmetric dihydroxylation and reduction reactions were used to control absolute configuration, was exploited in the preparation of a C2-symmetrical dipyranone. The homotopic dihydropyran (DHP) rings of this precursor were differentiated statistically using by a Prévost reaction and further functionalisation. A second Prévost reaction was used to functionalise the other DHP; global deprotection and peracetylation gave a protected version of the C58C71 fragment of palytoxin. Methods which might be of value in future synthetic work were developed for the stereoselective functionalisation of THP rings similar to those found in this fragment.

Graphical abstract: A two-directional synthesis of the C58–C71 fragment of palytoxin

Article information

Article type
Paper
Submitted
14 Jul 2003
Accepted
18 Nov 2003
First published
05 Jan 2004

Org. Biomol. Chem., 2004,2, 373-386

A two-directional synthesis of the C58C71 fragment of palytoxin

R. Hodgson and A. Nelson, Org. Biomol. Chem., 2004, 2, 373 DOI: 10.1039/B307950C

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