Synthesis and reactions of the pestalotiopsin skeleton

Thomas M. Baker; David J. Edmonds; Deborah Hamilton; Christopher J. O'Brien; David J. Procter

doi:10.1002/anie.200801900

Synthesis and reactions of the pestalotiopsin skeleton

Thomas M. Baker, David J. Edmonds, Deborah Hamilton, Christopher J. O'Brien, David J. Procter

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

Abstract

(Chemical Equation Presented) Family ties: The pestalotiopsin framework has been constructed by using a SmI2-mediated cyclization and a Nozaki-Hiyama-Kishi coupling to construct the four- and nine-membered rings of the target, respectively. The first synthetic entry into the previously unexplored taedolidol family of natural products has been achieved through a stereoselective, acid-mediated cyclization of the pestalotiopsin skeleton. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

Original language	English
Pages (from-to)	5631-5633
Number of pages	2
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	30
DOIs	https://doi.org/10.1002/anie.200801900
Publication status	Published - 14 Jul 2008

Keywords

Natural products
Pestalotiopsins
Samarium
Taedolidols
Total synthesis

Access to Document

10.1002/anie.200801900

http://www3.interscience.wiley.com/cgi-bin/fulltext/120081403/PDFSTART

CCDC 684818: Experimental Crystal Structure Determination
Baker, T. M. (Contributor), Edmonds, D. J. (Contributor), Hamilton, D. (Contributor), O'Brien, C. J. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2008
DOI: 10.5517/ccqzlx5, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccqzlx5&sid=DataCite
Dataset

Cite this

@article{02bf272a972848c0abcb7dadbd88b4a8,

title = "Synthesis and reactions of the pestalotiopsin skeleton",

abstract = "(Chemical Equation Presented) Family ties: The pestalotiopsin framework has been constructed by using a SmI2-mediated cyclization and a Nozaki-Hiyama-Kishi coupling to construct the four- and nine-membered rings of the target, respectively. The first synthetic entry into the previously unexplored taedolidol family of natural products has been achieved through a stereoselective, acid-mediated cyclization of the pestalotiopsin skeleton. {\textcopyright} 2008 Wiley-VCH Verlag GmbH & Co. KGaA.",

keywords = "Natural products, Pestalotiopsins, Samarium, Taedolidols, Total synthesis",

author = "Baker, {Thomas M.} and Edmonds, {David J.} and Deborah Hamilton and O'Brien, {Christopher J.} and Procter, {David J.}",

note = "Baker, Thomas M. Edmonds, David J. Hamilton, Deborah O'Brien, Christopher J. Procter, David J. 33 WILEY-V C H VERLAG GMBH WEINHEIM 328PG",

year = "2008",

month = jul,

day = "14",

doi = "10.1002/anie.200801900",

language = "English",

volume = "47",

pages = "5631--5633",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley & Sons Ltd",

number = "30",

}

TY - JOUR

T1 - Synthesis and reactions of the pestalotiopsin skeleton

AU - Baker, Thomas M.

AU - Edmonds, David J.

AU - Hamilton, Deborah

AU - O'Brien, Christopher J.

AU - Procter, David J.

N1 - Baker, Thomas M. Edmonds, David J. Hamilton, Deborah O'Brien, Christopher J. Procter, David J. 33 WILEY-V C H VERLAG GMBH WEINHEIM 328PG

PY - 2008/7/14

Y1 - 2008/7/14

N2 - (Chemical Equation Presented) Family ties: The pestalotiopsin framework has been constructed by using a SmI2-mediated cyclization and a Nozaki-Hiyama-Kishi coupling to construct the four- and nine-membered rings of the target, respectively. The first synthetic entry into the previously unexplored taedolidol family of natural products has been achieved through a stereoselective, acid-mediated cyclization of the pestalotiopsin skeleton. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

AB - (Chemical Equation Presented) Family ties: The pestalotiopsin framework has been constructed by using a SmI2-mediated cyclization and a Nozaki-Hiyama-Kishi coupling to construct the four- and nine-membered rings of the target, respectively. The first synthetic entry into the previously unexplored taedolidol family of natural products has been achieved through a stereoselective, acid-mediated cyclization of the pestalotiopsin skeleton. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

KW - Natural products

KW - Pestalotiopsins

KW - Samarium

KW - Taedolidols

KW - Total synthesis

U2 - 10.1002/anie.200801900

DO - 10.1002/anie.200801900

M3 - Article

SN - 1433-7851

VL - 47

SP - 5631

EP - 5633

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 30

ER -

Synthesis and reactions of the pestalotiopsin skeleton

Abstract

Keywords

Access to Document

Fingerprint

Datasets

CCDC 684818: Experimental Crystal Structure Determination

Cite this