A new and effective route to (+/-)-botryodiplodin and (+/-)-epi-botryodiplodin acetates using a halogen atom transfer Ueno-Stork cyclization

Laurent De Buyck; Cristina Forzato; Franco Ghelfi; Adele Mucci; Patrizia Nitti; Ugo M. Pagnoni; Andrew F. Parsons; Giuliana Pitacco; Fabrizio Roncaglia

doi:10.1016/j.tetlet.2006.08.121

A new and effective route to (+/-)-botryodiplodin and (+/-)-epi-botryodiplodin acetates using a halogen atom transfer Ueno-Stork cyclization

Laurent De Buyck, Cristina Forzato, Franco Ghelfi, Adele Mucci, Patrizia Nitti, Ugo M. Pagnoni, Andrew F. Parsons, Giuliana Pitacco, Fabrizio Roncaglia

Chemistry

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

Abstract

(+/-)-Botryodiplodin and (+/-)-epi-botryodiplodin acetates were prepared in good yields following a practical four step route. The method, for the construction of the strategic tetrahydrofuran ring, hinged on an unprecedented halogen atom transfer Ueno-Stork cyclization of an O-allyl alpha,alpha-dihalohemiacetal acetate, catalyzed by the redox complex CuCl/N,N,N ',N '',N ''-pentamethyldiethylenetriamine. (c) 2006 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	7759-7762
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	44
DOIs	https://doi.org/10.1016/j.tetlet.2006.08.121
Publication status	Published - 30 Oct 2006

Keywords

halocompounds
acetals
radical reactions
cyclization
Ueno-Stork
TRANSFER RADICAL CYCLIZATIONS
CHAETOMELLIC ANHYDRIDE-A
FUNCTIONAL REARRANGEMENT
PENICILLIUM-STIPITATUM
CLAISEN REARRANGEMENT
EFFICIENT ROUTE
BOTRYODIPLODIN
(-)-BOTRYODIPLODIN
STEREOCHEMISTRY
ROQUEFORTI

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10.1016/j.tetlet.2006.08.121

Cite this

@article{d61e5546302d4cd6b9bcaa488c09a94e,

title = "A new and effective route to (+/-)-botryodiplodin and (+/-)-epi-botryodiplodin acetates using a halogen atom transfer Ueno-Stork cyclization",

abstract = "(+/-)-Botryodiplodin and (+/-)-epi-botryodiplodin acetates were prepared in good yields following a practical four step route. The method, for the construction of the strategic tetrahydrofuran ring, hinged on an unprecedented halogen atom transfer Ueno-Stork cyclization of an O-allyl alpha,alpha-dihalohemiacetal acetate, catalyzed by the redox complex CuCl/N,N,N ',N '',N ''-pentamethyldiethylenetriamine. (c) 2006 Elsevier Ltd. All rights reserved.",

keywords = "halocompounds, acetals, radical reactions, cyclization, Ueno-Stork, TRANSFER RADICAL CYCLIZATIONS, CHAETOMELLIC ANHYDRIDE-A, FUNCTIONAL REARRANGEMENT, PENICILLIUM-STIPITATUM, CLAISEN REARRANGEMENT, EFFICIENT ROUTE, BOTRYODIPLODIN, (-)-BOTRYODIPLODIN, STEREOCHEMISTRY, ROQUEFORTI",

author = "{De Buyck}, Laurent and Cristina Forzato and Franco Ghelfi and Adele Mucci and Patrizia Nitti and Pagnoni, {Ugo M.} and Parsons, {Andrew F.} and Giuliana Pitacco and Fabrizio Roncaglia",

year = "2006",

month = oct,

day = "30",

doi = "10.1016/j.tetlet.2006.08.121",

language = "English",

volume = "47",

pages = "7759--7762",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "44",

}

TY - JOUR

T1 - A new and effective route to (+/-)-botryodiplodin and (+/-)-epi-botryodiplodin acetates using a halogen atom transfer Ueno-Stork cyclization

AU - De Buyck, Laurent

AU - Forzato, Cristina

AU - Ghelfi, Franco

AU - Mucci, Adele

AU - Nitti, Patrizia

AU - Pagnoni, Ugo M.

AU - Parsons, Andrew F.

AU - Pitacco, Giuliana

AU - Roncaglia, Fabrizio

PY - 2006/10/30

Y1 - 2006/10/30

N2 - (+/-)-Botryodiplodin and (+/-)-epi-botryodiplodin acetates were prepared in good yields following a practical four step route. The method, for the construction of the strategic tetrahydrofuran ring, hinged on an unprecedented halogen atom transfer Ueno-Stork cyclization of an O-allyl alpha,alpha-dihalohemiacetal acetate, catalyzed by the redox complex CuCl/N,N,N ',N '',N ''-pentamethyldiethylenetriamine. (c) 2006 Elsevier Ltd. All rights reserved.

AB - (+/-)-Botryodiplodin and (+/-)-epi-botryodiplodin acetates were prepared in good yields following a practical four step route. The method, for the construction of the strategic tetrahydrofuran ring, hinged on an unprecedented halogen atom transfer Ueno-Stork cyclization of an O-allyl alpha,alpha-dihalohemiacetal acetate, catalyzed by the redox complex CuCl/N,N,N ',N '',N ''-pentamethyldiethylenetriamine. (c) 2006 Elsevier Ltd. All rights reserved.

KW - halocompounds

KW - acetals

KW - radical reactions

KW - cyclization

KW - Ueno-Stork

KW - TRANSFER RADICAL CYCLIZATIONS

KW - CHAETOMELLIC ANHYDRIDE-A

KW - FUNCTIONAL REARRANGEMENT

KW - PENICILLIUM-STIPITATUM

KW - CLAISEN REARRANGEMENT

KW - EFFICIENT ROUTE

KW - BOTRYODIPLODIN

KW - (-)-BOTRYODIPLODIN

KW - STEREOCHEMISTRY

KW - ROQUEFORTI

U2 - 10.1016/j.tetlet.2006.08.121

DO - 10.1016/j.tetlet.2006.08.121

M3 - Article

VL - 47

SP - 7759

EP - 7762

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 44

ER -