Synthesis of 9- and 10-membered macrolactones by selective ozonolysis of 1,4-diazaphenanthrene derivatives

Elisa Pérez-Sacau; Jorge Soto-Delgado; Ana Estévez-Braun; Ángel G. Ravelo

doi:10.1016/j.tet.2004.10.075

Synthesis of 9- and 10-membered macrolactones by selective ozonolysis of 1,4-diazaphenanthrene derivatives

Elisa Pérez-Sacau, Jorge Soto-Delgado, Ana Estévez-Braun, Ángel G. Ravelo

Exact Sciences School

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

15 Citations (Scopus)

Abstract

9- and 10-membered macrolactones bearing benzo and diazine rings were obtained by chemoselective ozonolysis of dihydrofuran and pyran 1,4-diazaphenathrene derivatives. This is the first example of preparation of macrolactones by chemoselective ozonolysis of an enol double bond shared by aromatic and heterocyclic rings.

Original language	English
Pages (from-to)	437-445
Number of pages	9
Journal	Tetrahedron
Volume	61
Issue number	2
DOIs	https://doi.org/10.1016/j.tet.2004.10.075
Publication status	Published - 10 Jan 2005

Keywords

1,4-Diazaphenanthrene derivatives
9- and 10-membered macrolactones
Ozonolysis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2004.10.075

Cite this

@article{e7584ec2f39842398b3aaa74c8f7039f,

title = "Synthesis of 9- and 10-membered macrolactones by selective ozonolysis of 1,4-diazaphenanthrene derivatives",

abstract = "9- and 10-membered macrolactones bearing benzo and diazine rings were obtained by chemoselective ozonolysis of dihydrofuran and pyran 1,4-diazaphenathrene derivatives. This is the first example of preparation of macrolactones by chemoselective ozonolysis of an enol double bond shared by aromatic and heterocyclic rings.",

keywords = "1,4-Diazaphenanthrene derivatives, 9- and 10-membered macrolactones, Ozonolysis",

author = "Elisa P{\'e}rez-Sacau and Jorge Soto-Delgado and Ana Est{\'e}vez-Braun and Ravelo, {{\'A}ngel G.}",

note = "Funding Information: This work has been funded by Spanish MCYT (SAF2003-04200-C02-02) and by ICIC (Instituto Canario de Investigaciones del C{\'a}ncer). E.P.S. thanks the ICIC for a postdoctoral fellowship. The authors thank Dr. J. Platas for valuable discussions regarding the structures of lower-energy conformers. ",

year = "2005",

month = jan,

day = "10",

doi = "10.1016/j.tet.2004.10.075",

language = "English",

volume = "61",

pages = "437--445",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "2",

}

TY - JOUR

T1 - Synthesis of 9- and 10-membered macrolactones by selective ozonolysis of 1,4-diazaphenanthrene derivatives

AU - Pérez-Sacau, Elisa

AU - Soto-Delgado, Jorge

AU - Estévez-Braun, Ana

AU - Ravelo, Ángel G.

N1 - Funding Information: This work has been funded by Spanish MCYT (SAF2003-04200-C02-02) and by ICIC (Instituto Canario de Investigaciones del Cáncer). E.P.S. thanks the ICIC for a postdoctoral fellowship. The authors thank Dr. J. Platas for valuable discussions regarding the structures of lower-energy conformers.

PY - 2005/1/10

Y1 - 2005/1/10

N2 - 9- and 10-membered macrolactones bearing benzo and diazine rings were obtained by chemoselective ozonolysis of dihydrofuran and pyran 1,4-diazaphenathrene derivatives. This is the first example of preparation of macrolactones by chemoselective ozonolysis of an enol double bond shared by aromatic and heterocyclic rings.

AB - 9- and 10-membered macrolactones bearing benzo and diazine rings were obtained by chemoselective ozonolysis of dihydrofuran and pyran 1,4-diazaphenathrene derivatives. This is the first example of preparation of macrolactones by chemoselective ozonolysis of an enol double bond shared by aromatic and heterocyclic rings.

KW - 1,4-Diazaphenanthrene derivatives

KW - 9- and 10-membered macrolactones

KW - Ozonolysis

UR - http://www.scopus.com/inward/record.url?scp=9744247596&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2004.10.075

DO - 10.1016/j.tet.2004.10.075

M3 - Article

AN - SCOPUS:9744247596

SN - 0040-4020

VL - 61

SP - 437

EP - 445

JO - Tetrahedron

JF - Tetrahedron

IS - 2

ER -

Synthesis of 9- and 10-membered macrolactones by selective ozonolysis of 1,4-diazaphenanthrene derivatives

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this