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Proceedings of the National Academy of Sciences (PNAS)

Proceedings of the National Academy of Sciences of the United States of America

, том 101 , издание 33 , страницы 11955-11959

Total synthesis of (–)-spinosyn A

Тип публикации: Journal Article

Дата публикации: 2004-06-11

Proceedings of the National Academy of Sciences (PNAS)

Proceedings of the National Academy of Sciences of the United States of America

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SJR: 3.414

CiteScore: 16.5

Impact factor: 9.1

ISSN: 00278424, 10916490

DOI: 10.1073/pnas.0401247101

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PubMed ID: 15173590

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A convergent, highly stereoselective total synthesis of (–)-spinosyn A ( 1 ) is described. Key features of the synthesis include the transannular Diels–Alder reaction of macrocyclic pentaene 11 and the transannular Morita–Baylis–Hillman cyclization of 12 that generates tetracycle 26. The total synthesis of (–)-spinosyn A was completed by a sequence involving the highly β-selective glycosidation reaction of 13 and glycosyl imidate 30.

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Mergott D. J., Frank S. A., Roush W. R. Total synthesis of (–)-spinosyn A // Proceedings of the National Academy of Sciences of the United States of America. 2004. Vol. 101. No. 33. pp. 11955-11959.

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TY - JOUR

DO - 10.1073/pnas.0401247101

UR - https://doi.org/10.1073/pnas.0401247101

TI - Total synthesis of (–)-spinosyn A

T2 - Proceedings of the National Academy of Sciences of the United States of America

AU - Mergott, Dustin J.

AU - Frank, Scott A

AU - Roush, William R.

PY - 2004

DA - 2004/06/11

PB - Proceedings of the National Academy of Sciences (PNAS)

SP - 11955-11959

IS - 33

VL - 101

PMID - 15173590

SN - 0027-8424

SN - 1091-6490

ER -

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@article{2004_Mergott,

author = {Dustin J. Mergott and Scott A Frank and William R. Roush},

title = {Total synthesis of (–)-spinosyn A},

journal = {Proceedings of the National Academy of Sciences of the United States of America},

year = {2004},

volume = {101},

publisher = {Proceedings of the National Academy of Sciences (PNAS)},

month = {jun},

url = {https://doi.org/10.1073/pnas.0401247101},

number = {33},

pages = {11955--11959},

doi = {10.1073/pnas.0401247101}

}

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Mergott, Dustin J., et al. “Total synthesis of (–)-spinosyn A.” Proceedings of the National Academy of Sciences of the United States of America, vol. 101, no. 33, Jun. 2004, pp. 11955-11959. https://doi.org/10.1073/pnas.0401247101.

Издатель

Proceedings of the National Academy of Sciences (PNAS)

Журнал

Proceedings of the National Academy of Sciences of the United States of America

scimago Q1

wos Q1

БС1

SJR

3.414

CiteScore

16.5

Impact factor

9.1

ISSN

00278424 (Print)

10916490 (Electronic)