Direct synthesis of pyran-lactones related to naphthoquinoneantibiotics

M. F. Semmelhack; Christina Bodurow; Mary Baum

doi:10.1016/S0040-4039(01)91000-7

Direct synthesis of pyran-lactones related to naphthoquinoneantibiotics

M. F. Semmelhack, Christina Bodurow, Mary Baum

Chemistry

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

77 Scopus citations

Abstract

Simple benzopyrans with a fused γ-lactone unit are prepared from an o-disubstituted arene by direct intramolecular alkoxycarbonylation/lactonization promoted by palladium diacetate; the process gives high yields and moderate stereoselectivity, favoring the cis lactone over trans by a factor of 5:1.

Original language	English (US)
Pages (from-to)	3171-3174
Number of pages	4
Journal	Tetrahedron Letters
Volume	25
Issue number	30
DOIs	https://doi.org/10.1016/S0040-4039(01)91000-7
State	Published - 1984

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)91000-7

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title = "Direct synthesis of pyran-lactones related to naphthoquinoneantibiotics",

abstract = "Simple benzopyrans with a fused γ-lactone unit are prepared from an o-disubstituted arene by direct intramolecular alkoxycarbonylation/lactonization promoted by palladium diacetate; the process gives high yields and moderate stereoselectivity, favoring the cis lactone over trans by a factor of 5:1.",

author = "Semmelhack, \{M. F.\} and Christina Bodurow and Mary Baum",

year = "1984",

doi = "10.1016/S0040-4039(01)91000-7",

language = "English (US)",

volume = "25",

pages = "3171--3174",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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number = "30",

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T1 - Direct synthesis of pyran-lactones related to naphthoquinoneantibiotics

AU - Semmelhack, M. F.

AU - Bodurow, Christina

AU - Baum, Mary

PY - 1984

Y1 - 1984

N2 - Simple benzopyrans with a fused γ-lactone unit are prepared from an o-disubstituted arene by direct intramolecular alkoxycarbonylation/lactonization promoted by palladium diacetate; the process gives high yields and moderate stereoselectivity, favoring the cis lactone over trans by a factor of 5:1.

AB - Simple benzopyrans with a fused γ-lactone unit are prepared from an o-disubstituted arene by direct intramolecular alkoxycarbonylation/lactonization promoted by palladium diacetate; the process gives high yields and moderate stereoselectivity, favoring the cis lactone over trans by a factor of 5:1.

UR - https://www.scopus.com/pages/publications/0021249894

UR - https://www.scopus.com/inward/citedby.url?scp=0021249894&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)91000-7

DO - 10.1016/S0040-4039(01)91000-7

M3 - Article

AN - SCOPUS:0021249894

SN - 0040-4039

VL - 25

SP - 3171

EP - 3174

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 30

ER -

Direct synthesis of pyran-lactones related to naphthoquinoneantibiotics

Abstract

All Science Journal Classification (ASJC) codes

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