Organic Letters, volume 9, issue 17, pages 3241-3243

Enantiospecific Total Synthesis of (−)-Bakkenolide III and Formal Total Synthesis of (−)-Bakkenolides B, C, H, L, V, and X

Chiao Hua Jiang ¹

Annyt Bhattacharyya ¹

Chin-Kang Sha ¹

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Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan, ROC |

Publication type: Journal Article

Publication date: 2007-07-24

American Chemical Society (ACS)

Journal: Organic Letters

scimago Q1

SJR: 1.245

CiteScore: 9.3

Impact factor: 4.9

ISSN: 15237060, 15237052

DOI: 10.1021/ol071124k

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PubMed ID: 17645346

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

A concise enantiospecific synthesis of (-)-bakkenolide III was accomplished from (S)-(+)-carvone. The key step involved radical cyclization of an iodoketone intermediate which afforded the cis-hydrindanone skeleton. Further synthetic transformations generated bakkenolide III, which also constitutes the formal total synthesis of (-)-bakkenolides, B, C, H, L, V, and X.

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CITATIONS

39 Total citations

5 Recent citations

4.26 Field Citation Ratio

0.76 Relative Citation Ratio

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Jiang C. H., Bhattacharyya A., Sha C. Enantiospecific Total Synthesis of (−)-Bakkenolide III and Formal Total Synthesis of (−)-Bakkenolides B, C, H, L, V, and X // Organic Letters. 2007. Vol. 9. No. 17. pp. 3241-3243.

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RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/ol071124k

UR - https://doi.org/10.1021/ol071124k

TI - Enantiospecific Total Synthesis of (−)-Bakkenolide III and Formal Total Synthesis of (−)-Bakkenolides B, C, H, L, V, and X

T2 - Organic Letters

AU - Jiang, Chiao Hua

AU - Bhattacharyya, Annyt

AU - Sha, Chin-Kang

PY - 2007

DA - 2007/07/24

PB - American Chemical Society (ACS)

SP - 3241-3243

IS - 17

VL - 9

PMID - 17645346

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

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@article{2007_Jiang,

author = {Chiao Hua Jiang and Annyt Bhattacharyya and Chin-Kang Sha},

title = {Enantiospecific Total Synthesis of (−)-Bakkenolide III and Formal Total Synthesis of (−)-Bakkenolides B, C, H, L, V, and X},

journal = {Organic Letters},

year = {2007},

volume = {9},

publisher = {American Chemical Society (ACS)},

month = {jul},

url = {https://doi.org/10.1021/ol071124k},

number = {17},

pages = {3241--3243},

doi = {10.1021/ol071124k}

}

MLA

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MLA Copy

Jiang, Chiao Hua, et al. “Enantiospecific Total Synthesis of (−)-Bakkenolide III and Formal Total Synthesis of (−)-Bakkenolides B, C, H, L, V, and X.” Organic Letters, vol. 9, no. 17, Jul. 2007, pp. 3241-3243. https://doi.org/10.1021/ol071124k.

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Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

SJR

1.245

CiteScore

9.3

Impact factor

4.9

ISSN

15237060 (Print)

15237052 (Electronic)