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Corrigendum to “Approaches to the total synthesis of phomactins”: [Tetrahedron Lett. 44 (2003) 2713]

✍ Scribed by Andrew S Balnaves; Graham McGowan; Peter D.P Shapland; Eric J Thomas

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 56 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)00880-3

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✦ Synopsis

Footnote 5 of the above Tetrahedron Letter states that ''The spontaneous rearrangement of Sch. 49028 into phomactin A was observed by Pattenden et al. during their synthesis, see ref. 4. 1 '' However, it should be made absolutely clear that Goldring and Pattenden did not state in their paper 1 that Sch. 49028 spontaneously rearranged into phomactin A. These authors did not isolate Sch. 49028 (still attributed the originally assigned 2 hydroxy-epoxide structure 1 in the above Tetrahedron Letter) and could not therefore study its rearrangement.

In the final step of their synthesis of phomactin A 2, 1 Goldring and Pattenden deprotected the bis-p-methoxybenzyl ether 3 and isolated phomactin A 2 directly. They did not isolate the hydroxyepoxide 1 (Sch. 49028?) although it may be an intermediate in the conversion of 3 into 2. Moreover, there is some doubt as to whether the compound identified as Sch. 49028 was correctly identified originally 2 as the hydroxyepoxide 1 or whether it should have been identified as phomactin A 2 since the NMR spectrum reported for Sch. 49028 2 in deuterated chloroform was found by both Pattenden 1 and Halcomb 3 to correspond to that of synthetic phomactin A 2.

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