Synthesis, structure revision, and absolute configuration of (+)-didemniserinolipid B, a serinol marine natural product from a tunicate Didemnum sp.

Hiromasa Kiyota; Darren J. Dixon; Christine K. Luscombe; Stephan Hettstedt; Steven V. Ley

doi:10.1021/ol026421y

Synthesis, structure revision, and absolute configuration of (+)-didemniserinolipid B, a serinol marine natural product from a tunicate Didemnum sp.

Hiromasa Kiyota, Darren J. Dixon, Christine K. Luscombe, Stephan Hettstedt, Steven V. Ley

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

59 Citations (Scopus)

Abstract

equation presented Didemniserinolipid B (1) R = H; proposed structure R = SO₃Na; revised structure En route to proving the absolute and relative stereochemistry, through synthesis, of (+)-didemniserinolipid B (1), the first natural serinolipid isolated from a tunicate Didemnum sp., it was discovered that the isolated natural product was in fact the 31-sulfate configured 8R,9R,10R,-13S,30S. This structural reassignment was only possible after the development of a microwave-assisted method for the sulfation of unreactive hydroxyl groups.

Original language	English
Pages (from-to)	3223-3226
Number of pages	4
Journal	Organic letters
Volume	4
Issue number	19
DOIs	https://doi.org/10.1021/ol026421y
Publication status	Published - 2002 Sept 19

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "equation presented Didemniserinolipid B (1) R = H; proposed structure R = SO3Na; revised structure En route to proving the absolute and relative stereochemistry, through synthesis, of (+)-didemniserinolipid B (1), the first natural serinolipid isolated from a tunicate Didemnum sp., it was discovered that the isolated natural product was in fact the 31-sulfate configured 8R,9R,10R,-13S,30S. This structural reassignment was only possible after the development of a microwave-assisted method for the sulfation of unreactive hydroxyl groups.",

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AU - Hettstedt, Stephan

AU - Ley, Steven V.

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Synthesis, structure revision, and absolute configuration of (+)-didemniserinolipid B, a serinol marine natural product from a tunicate Didemnum sp.

Abstract

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UN SDGs

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