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

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	3
Journal	Organic Letters
Volume	4
Issue number	19
DOIs	https://doi.org/10.1021/ol026421y
Publication status	Published - 19 Sept 2002

Keywords

Microwave (irradn.; prepn. of (+)-didemniserinolipid B via microwave-assisted sulfation and revision of its abs. configuration); Absolute configuration; Asymmetric synthesis and induction; Sulfation (prepn. of (+)-didemniserinolipid B via microwave-assisted sulfation and revision of its abs. configuration)

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

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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author = "Hiromasa Kiyota and Dixon, {Darren J.} and Luscombe, {Christine K.} and Stephan Hettstedt and Ley, {Steven V.}",

year = "2002",

month = sep,

day = "19",

doi = "10.1021/ol026421y",

language = "English",

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journal = "Organic Letters",

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T1 - Synthesis, structure revision, and absolute configuration of (+)-didemniserinolipid B, a serinol marine natural product from a tunicate Didemnum sp.

AU - Kiyota, Hiromasa

AU - Dixon, Darren J.

AU - Luscombe, Christine K.

AU - Hettstedt, Stephan

AU - Ley, Steven V.

PY - 2002/9/19

Y1 - 2002/9/19

N2 - 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.

AB - 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.

KW - Microwave (irradn.; prepn. of (+)-didemniserinolipid B via microwave-assisted sulfation and revision of its abs. configuration); Absolute configuration; Asymmetric synthesis and induction; Sulfation (prepn. of (+)-didemniserinolipid B via microwave-assist

U2 - 10.1021/ol026421y

DO - 10.1021/ol026421y

M3 - Article

SN - 1523-7052

VL - 4

SP - 3223

EP - 3226

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

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

Abstract

Keywords

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