Organic Letters, volume 8, issue 25, pages 5901-5904

Exploring Biosynthetic Relationships among Furanocembranoids: Synthesis of (−)-Bipinnatin J, (+)-Intricarene, (+)-Rubifolide, and (+)-Isoepilophodione B

Paul A Roethle ¹

Paul T Hernandez ¹

Dirk Trauner ¹

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Department of Chemistry, University of California, Berkeley, California 94720 |

Publication type: Journal Article

Publication date: 2006-11-09

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/ol062581o

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PubMed ID: 17134301

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

The asymmetric total synthesis of (-)-bipinnatin J and its conversion into (+)-intricarene through a transannular 1,3-dipolar cycloaddition is described. In addition, the conversion of (-)-bipinnatin J into (+)-rubifolide and (+)-isoepilophodione B is reported. Biosynthetic relationships among furanocembranoids and the possible role of 1,3-dipolar cycloadditions in biosynthesis are discussed. [reaction: see text]

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Roethle P. A., Hernandez P. T., Trauner D. Exploring Biosynthetic Relationships among Furanocembranoids: Synthesis of (−)-Bipinnatin J, (+)-Intricarene, (+)-Rubifolide, and (+)-Isoepilophodione B // Organic Letters. 2006. Vol. 8. No. 25. pp. 5901-5904.

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RIS Copy

TY - JOUR

DO - 10.1021/ol062581o

UR - https://doi.org/10.1021/ol062581o

TI - Exploring Biosynthetic Relationships among Furanocembranoids: Synthesis of (−)-Bipinnatin J, (+)-Intricarene, (+)-Rubifolide, and (+)-Isoepilophodione B

T2 - Organic Letters

AU - Roethle, Paul A

AU - Hernandez, Paul T

AU - Trauner, Dirk

PY - 2006

DA - 2006/11/09

PB - American Chemical Society (ACS)

SP - 5901-5904

IS - 25

VL - 8

PMID - 17134301

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

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@article{2006_Roethle,

author = {Paul A Roethle and Paul T Hernandez and Dirk Trauner},

title = {Exploring Biosynthetic Relationships among Furanocembranoids: Synthesis of (−)-Bipinnatin J, (+)-Intricarene, (+)-Rubifolide, and (+)-Isoepilophodione B},

journal = {Organic Letters},

year = {2006},

volume = {8},

publisher = {American Chemical Society (ACS)},

month = {nov},

url = {https://doi.org/10.1021/ol062581o},

number = {25},

pages = {5901--5904},

doi = {10.1021/ol062581o}

}

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Roethle, Paul A., et al. “Exploring Biosynthetic Relationships among Furanocembranoids: Synthesis of (−)-Bipinnatin J, (+)-Intricarene, (+)-Rubifolide, and (+)-Isoepilophodione B.” Organic Letters, vol. 8, no. 25, Nov. 2006, pp. 5901-5904. https://doi.org/10.1021/ol062581o.

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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)