Synthesis of Unsymmetrical Dithioacetals: An Efficient Synthesis of a Novel LTD4 Antagonist, L-660,711

J. M. McNamara; J. L. Leazer; M. Bhupathy; J. S. Amato; R. A. Reamer; P. J. Reider; E. J.J. Grabowski

doi:10.1021/jo00276a038

Synthesis of Unsymmetrical Dithioacetals: An Efficient Synthesis of a Novel LTD₄ Antagonist, L-660,711

J. M. McNamara, J. L. Leazer, M. Bhupathy, J. S. Amato, R. A. Reamer, P. J. Reider, E. J.J. Grabowski

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

55 Scopus citations

Abstract

An efficient four-step synthesis of the potent LTD₄ antagonist L-660,711 (1) is described. The key step involves selective conversion of aldehyde 2 to the unsymmetrical dithioacetal 7, via O-trimethylsilyl hemithioacetal 10. This specific cleavage of the carbon-oxygen bond of a mixed 0,S-acetal permits the unprecedented synthesis of unsymmetrical dithioacetals.

Original language	English (US)
Pages (from-to)	3718-3721
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	54
Issue number	15
DOIs	https://doi.org/10.1021/jo00276a038
State	Published - Jul 1 1989
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00276a038

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title = "Synthesis of Unsymmetrical Dithioacetals: An Efficient Synthesis of a Novel LTD4 Antagonist, L-660,711",

abstract = "An efficient four-step synthesis of the potent LTD4 antagonist L-660,711 (1) is described. The key step involves selective conversion of aldehyde 2 to the unsymmetrical dithioacetal 7, via O-trimethylsilyl hemithioacetal 10. This specific cleavage of the carbon-oxygen bond of a mixed 0,S-acetal permits the unprecedented synthesis of unsymmetrical dithioacetals.",

author = "McNamara, {J. M.} and Leazer, {J. L.} and M. Bhupathy and Amato, {J. S.} and Reamer, {R. A.} and Reider, {P. J.} and Grabowski, {E. J.J.}",

year = "1989",

month = jul,

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doi = "10.1021/jo00276a038",

language = "English (US)",

volume = "54",

pages = "3718--3721",

journal = "Journal of Organic Chemistry",

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publisher = "American Chemical Society",

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T1 - Synthesis of Unsymmetrical Dithioacetals

T2 - An Efficient Synthesis of a Novel LTD4 Antagonist, L-660,711

AU - McNamara, J. M.

AU - Leazer, J. L.

AU - Bhupathy, M.

AU - Amato, J. S.

AU - Reamer, R. A.

AU - Reider, P. J.

AU - Grabowski, E. J.J.

PY - 1989/7/1

Y1 - 1989/7/1

N2 - An efficient four-step synthesis of the potent LTD4 antagonist L-660,711 (1) is described. The key step involves selective conversion of aldehyde 2 to the unsymmetrical dithioacetal 7, via O-trimethylsilyl hemithioacetal 10. This specific cleavage of the carbon-oxygen bond of a mixed 0,S-acetal permits the unprecedented synthesis of unsymmetrical dithioacetals.

AB - An efficient four-step synthesis of the potent LTD4 antagonist L-660,711 (1) is described. The key step involves selective conversion of aldehyde 2 to the unsymmetrical dithioacetal 7, via O-trimethylsilyl hemithioacetal 10. This specific cleavage of the carbon-oxygen bond of a mixed 0,S-acetal permits the unprecedented synthesis of unsymmetrical dithioacetals.

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U2 - 10.1021/jo00276a038

DO - 10.1021/jo00276a038

M3 - Article

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VL - 54

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

Synthesis of Unsymmetrical Dithioacetals: An Efficient Synthesis of a Novel LTD₄ Antagonist, L-660,711

Abstract

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