Synthesis of macrocyclic ketoesters by an n + 1 strategy based on free-radical carbonylation

Kiyoto Nagahara; Ilhyong Ryu; Hiroshi Yamazaki; Nobuaki Kambe; Mitsuo Komatsu; Noboru Sonoda; Akio Baba

doi:10.1016/S0040-4020(97)01048-X

Synthesis of macrocyclic ketoesters by an n + 1 strategy based on free-radical carbonylation

Kiyoto Nagahara, Ilhyong Ryu, Hiroshi Yamazaki, Nobuaki Kambe, Mitsuo Komatsu, Noboru Sonoda, Akio Baba

Department of Applied Chemistry

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

20 Scopus citations

Abstract

The synthesis of 10-17 membered 4-oxolactones 2 from alkyl iodides 1 having an acryloxy moiety at the termini, carbon monoxide, and TTMSS (or tin hydride) was achieved under free radical reaction conditions. The allyltin mediated reaction of 1 also proceeded successfully to furnish 2-allyl-substituted 4-oxolactones 3 in moderate to good yields. In this n + 1 type macrocyclization, high dilution conditions ([1] = 0.005-0.01 M) are beneficial for both the intermolecular trapping of CO and the intramolecular acyl radical addition to the C-C double bond.

Original language	English
Pages (from-to)	14615-14626
Number of pages	12
Journal	Tetrahedron
Volume	53
Issue number	43
DOIs	https://doi.org/10.1016/S0040-4020(97)01048-X
State	Published - 27 Oct 1997

Access to Document

10.1016/S0040-4020(97)01048-X

Fingerprint Dive into the research topics of 'Synthesis of macrocyclic ketoesters by an n + 1 strategy based on free-radical carbonylation'. Together they form a unique fingerprint.

Cite this

@article{97bcc6e81fca43ca9fff2996d1f15599,

title = "Synthesis of macrocyclic ketoesters by an n + 1 strategy based on free-radical carbonylation",

abstract = "The synthesis of 10-17 membered 4-oxolactones 2 from alkyl iodides 1 having an acryloxy moiety at the termini, carbon monoxide, and TTMSS (or tin hydride) was achieved under free radical reaction conditions. The allyltin mediated reaction of 1 also proceeded successfully to furnish 2-allyl-substituted 4-oxolactones 3 in moderate to good yields. In this n + 1 type macrocyclization, high dilution conditions ([1] = 0.005-0.01 M) are beneficial for both the intermolecular trapping of CO and the intramolecular acyl radical addition to the C-C double bond.",

author = "Kiyoto Nagahara and Ilhyong Ryu and Hiroshi Yamazaki and Nobuaki Kambe and Mitsuo Komatsu and Noboru Sonoda and Akio Baba",

year = "1997",

month = oct,

day = "27",

doi = "10.1016/S0040-4020(97)01048-X",

language = "English",

volume = "53",

pages = "14615--14626",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "43",

}

TY - JOUR

T1 - Synthesis of macrocyclic ketoesters by an n + 1 strategy based on free-radical carbonylation

AU - Nagahara, Kiyoto

AU - Ryu, Ilhyong

AU - Yamazaki, Hiroshi

AU - Kambe, Nobuaki

AU - Komatsu, Mitsuo

AU - Sonoda, Noboru

AU - Baba, Akio

PY - 1997/10/27

Y1 - 1997/10/27

N2 - The synthesis of 10-17 membered 4-oxolactones 2 from alkyl iodides 1 having an acryloxy moiety at the termini, carbon monoxide, and TTMSS (or tin hydride) was achieved under free radical reaction conditions. The allyltin mediated reaction of 1 also proceeded successfully to furnish 2-allyl-substituted 4-oxolactones 3 in moderate to good yields. In this n + 1 type macrocyclization, high dilution conditions ([1] = 0.005-0.01 M) are beneficial for both the intermolecular trapping of CO and the intramolecular acyl radical addition to the C-C double bond.

AB - The synthesis of 10-17 membered 4-oxolactones 2 from alkyl iodides 1 having an acryloxy moiety at the termini, carbon monoxide, and TTMSS (or tin hydride) was achieved under free radical reaction conditions. The allyltin mediated reaction of 1 also proceeded successfully to furnish 2-allyl-substituted 4-oxolactones 3 in moderate to good yields. In this n + 1 type macrocyclization, high dilution conditions ([1] = 0.005-0.01 M) are beneficial for both the intermolecular trapping of CO and the intramolecular acyl radical addition to the C-C double bond.

UR - http://www.scopus.com/inward/record.url?scp=0343990734&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(97)01048-X

DO - 10.1016/S0040-4020(97)01048-X

M3 - Article

AN - SCOPUS:0343990734

VL - 53

SP - 14615

EP - 14626

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 43

ER -

Synthesis of macrocyclic ketoesters by an n + 1 strategy based on free-radical carbonylation

Abstract

Access to Document

Other files and links

Cite this