Multicomponent Coupling Approach to (±)-Frondosin B and a Ring-Expanded Analogue

Daniel J. Kerr; Anthony C. Willis; Bernard L. Flynn

doi:10.1021/ol035822q

Multicomponent Coupling Approach to (±)-Frondosin B and a Ring-Expanded Analogue

Daniel J. Kerr, Anthony C. Willis, Bernard L. Flynn^*

^*Corresponding author for this work

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

78 Citations (Scopus)

Abstract

(Equation presented) A recently discovered multicomponent coupling reaction is used to give direct access to a late intermediate in the synthesis of frondosin B. This intermediate can also be efficiently converted to a ring-expanded analogue of frondosin B by sustained heating of the reaction mixture. An unprecedented tandem 1,7-hydrogen shift, 8π-electrocyclization is proposed to explain the formation of this ring-expanded species.

Original language	English
Pages (from-to)	457-460
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	4
DOIs	https://doi.org/10.1021/ol035822q
Publication status	Published - 19 Feb 2004

Access to Document

10.1021/ol035822q

Cite this

@article{2bdb98baf98742b1880970061cff5034,

title = "Multicomponent Coupling Approach to (±)-Frondosin B and a Ring-Expanded Analogue",

abstract = "(Equation presented) A recently discovered multicomponent coupling reaction is used to give direct access to a late intermediate in the synthesis of frondosin B. This intermediate can also be efficiently converted to a ring-expanded analogue of frondosin B by sustained heating of the reaction mixture. An unprecedented tandem 1,7-hydrogen shift, 8π-electrocyclization is proposed to explain the formation of this ring-expanded species.",

author = "Kerr, \{Daniel J.\} and Willis, \{Anthony C.\} and Flynn, \{Bernard L.\}",

year = "2004",

month = feb,

day = "19",

doi = "10.1021/ol035822q",

language = "English",

volume = "6",

pages = "457--460",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "4",

}

TY - JOUR

T1 - Multicomponent Coupling Approach to (±)-Frondosin B and a Ring-Expanded Analogue

AU - Kerr, Daniel J.

AU - Willis, Anthony C.

AU - Flynn, Bernard L.

PY - 2004/2/19

Y1 - 2004/2/19

N2 - (Equation presented) A recently discovered multicomponent coupling reaction is used to give direct access to a late intermediate in the synthesis of frondosin B. This intermediate can also be efficiently converted to a ring-expanded analogue of frondosin B by sustained heating of the reaction mixture. An unprecedented tandem 1,7-hydrogen shift, 8π-electrocyclization is proposed to explain the formation of this ring-expanded species.

AB - (Equation presented) A recently discovered multicomponent coupling reaction is used to give direct access to a late intermediate in the synthesis of frondosin B. This intermediate can also be efficiently converted to a ring-expanded analogue of frondosin B by sustained heating of the reaction mixture. An unprecedented tandem 1,7-hydrogen shift, 8π-electrocyclization is proposed to explain the formation of this ring-expanded species.

UR - https://www.scopus.com/pages/publications/1342311527

U2 - 10.1021/ol035822q

DO - 10.1021/ol035822q

M3 - Article

SN - 1523-7060

VL - 6

SP - 457

EP - 460

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

Multicomponent Coupling Approach to (±)-Frondosin B and a Ring-Expanded Analogue

Abstract

Access to Document

Other files and links

Fingerprint

Cite this