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Minor carbonimidic dichlorides from the marine sponge pseudaxinyssa pitys

✍ Scribed by Stephen J. Wratten; D.John Faulkner


Book ID
104245607
Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
333 KB
Volume
19
Category
Article
ISSN
0040-4039

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✦ Synopsis


In the previous paper, 1 we described the structural elucidation by single crystal X-ray diffraction analysis of a third carbonimidic dichloride ?; from the Indo-Pacific sponge Pseudaxinyssa pitys. From the same sponge we have isolated three minor metabolites, all of which contained the carbonimidic dichloride functionality. Although we have been unable to interconvert these molecules because of their instability under most reaction conditions, analysis of the spectral data has provided sufficient information to allow us to suggest the most likely structures. In this paper, we wish to report the structural elucidation from spectral data of three additional carbonimidic dichlorides. Selected fractions from a silica gel chromatography of the chloroformsoluble material from a methanolic extract of P. -pitys were rechromatographed by HPLC on u-porasil to obtain the carbonimidic dichlorides l_ (0.25% dry weight), 2 (0.08% dry weight), ,3 (0.08% dry weight) and 5 (0.02% dry weight). Spin decoupling experiments allowed us to assign every signal in the 1 H nmr spectrum of carbonimidic dichloride 1 _-Similar decoupling experiments on the 'H nmr spectra of compounds 2 -2 allowed most of the signals in each spectrum to be assigned (Table 1). Carbonimidic dichloride 2 had the molecular formula C16H22NCC13, isomeric with 1. The infrared, ultraviolet, and mass spectra of z2 were almost identical


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We have recently described the isolation and structural elucidation of two carbonimidic dichlorides l\_ and 2 from the Indo-Pacific sponge Pseudaxinyssa pitys. 2 In this and the following paper3 we wish to describe the structural elucidation of the minor metabolites of P pitys. This paper describes