A total synthesis of (+/-)-phomactin A

C.M. Diaper; William Goldring; G. Pattenden

doi:10.1039/b307986d

A total synthesis of (+/-)-phomactin A

C.M. Diaper, William Goldring, G. Pattenden

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

44 Citations (Scopus)

Abstract

A total synthesis of the PAF antagonist phomactin A (1), isolated from the marine fungus Phoma sp. is described. The synthesis is based on a Cr(II)/Ni(II) macrocyclisation from the aldehyde vinyl iodide 14, leading to the key phomactatrienol intermediate 16a, followed by elaboration of 16a to the epoxyketone 21, which undergoes spontaneous pyran and hemiacetal ring formation to 1 on deprotection with DDQ.

Original language	English
Pages (from-to)	3949-3956
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	1
Issue number	22
DOIs	https://doi.org/10.1039/b307986d
Publication status	Published - 21 Nov 2003

ASJC Scopus subject areas

Biochemistry, Genetics and Molecular Biology(all)
Chemistry(all)

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10.1039/b307986d

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abstract = "A total synthesis of the PAF antagonist phomactin A (1), isolated from the marine fungus Phoma sp. is described. The synthesis is based on a Cr(II)/Ni(II) macrocyclisation from the aldehyde vinyl iodide 14, leading to the key phomactatrienol intermediate 16a, followed by elaboration of 16a to the epoxyketone 21, which undergoes spontaneous pyran and hemiacetal ring formation to 1 on deprotection with DDQ.",

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A total synthesis of (+/-)-phomactin A

Abstract

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