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 journalArticle

57 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 languageEnglish
Pages (from-to)3223-3226
Number of pages4
JournalOrganic Letters
Volume4
Issue number19
DOIs
Publication statusPublished - Sep 19 2002
Externally publishedYes

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sulfation
Urochordata
stereochemistry
Biological Products
sulfates
routes
microwaves
Stereochemistry
synthesis
products
Microwaves
configurations
Hydroxyl Radical
Sulfates
didemniserinolipid B
serinol

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Synthesis, structure revision, and absolute configuration of (+)-didemniserinolipid B, a serinol marine natural product from a tunicate Didemnum sp. / Kiyota, Hiromasa; Dixon, Darren J.; Luscombe, Christine K.; Hettstedt, Stephan; Ley, Steven V.

In: Organic Letters, Vol. 4, No. 19, 19.09.2002, p. 3223-3226.

Research output: Contribution to journalArticle

Kiyota, Hiromasa ; Dixon, Darren J. ; Luscombe, Christine K. ; Hettstedt, Stephan ; Ley, Steven V. / Synthesis, structure revision, and absolute configuration of (+)-didemniserinolipid B, a serinol marine natural product from a tunicate Didemnum sp. In: Organic Letters. 2002 ; Vol. 4, No. 19. pp. 3223-3226.
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