THE STEREOSELECTIVE SYNTHESIS OF UNSATURATED 9-MEMBERED LACTONES USING THE MALHERBE-BELLUS VARIANT OF THE CLAISEN REARRANGEMENT

M R  KLING; G A  MCNAUGHTONSMITH; R J K  TAYLOR

THE STEREOSELECTIVE SYNTHESIS OF UNSATURATED 9-MEMBERED LACTONES USING THE MALHERBE-BELLUS VARIANT OF THE CLAISEN REARRANGEMENT

M R KLING, G A MCNAUGHTONSMITH, R J K TAYLOR

Chemistry

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

Abstract

The title reaction has been used to prepare nine-membered lactones commencing from 2-vinyltetrahydrofurans and dichloroketene; the resulting DELTA5-dichlorolactones are exclusively trans but dechlorination using Bu3SnH-AIBN (azoisobutyronitrile) achieves concomitant isomerisation to give the cis-unsaturated lactones.

Original language	English
Pages (from-to)	1593-1595
Number of pages	3
Journal	JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS
Issue number	21
Publication status	Published - 7 Nov 1993

Keywords

HALICHONDRIA-OKADAI KADOTA
PRELIMINARY COMMUNICATION
ORGANOMETALLIC REAGENTS
MACROLIDE ANTIBIOTICS
MACROCYCLIC LACTONES
NEOHALICHOLACTONE
OBTUSENYNE

Cite this

@article{13c4bc0bf6cd44c4b243fee18e7206dd,

title = "THE STEREOSELECTIVE SYNTHESIS OF UNSATURATED 9-MEMBERED LACTONES USING THE MALHERBE-BELLUS VARIANT OF THE CLAISEN REARRANGEMENT",

abstract = "The title reaction has been used to prepare nine-membered lactones commencing from 2-vinyltetrahydrofurans and dichloroketene; the resulting DELTA5-dichlorolactones are exclusively trans but dechlorination using Bu3SnH-AIBN (azoisobutyronitrile) achieves concomitant isomerisation to give the cis-unsaturated lactones.",

keywords = "HALICHONDRIA-OKADAI KADOTA, PRELIMINARY COMMUNICATION, ORGANOMETALLIC REAGENTS, MACROLIDE ANTIBIOTICS, MACROCYCLIC LACTONES, NEOHALICHOLACTONE, OBTUSENYNE",

author = "KLING, {M R} and MCNAUGHTONSMITH, {G A} and TAYLOR, {R J K}",

year = "1993",

month = nov,

day = "7",

language = "English",

pages = "1593--1595",

journal = "JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS",

issn = "0022-4936",

publisher = "Chemical Society",

number = "21",

}

TY - JOUR

T1 - THE STEREOSELECTIVE SYNTHESIS OF UNSATURATED 9-MEMBERED LACTONES USING THE MALHERBE-BELLUS VARIANT OF THE CLAISEN REARRANGEMENT

AU - KLING, M R

AU - MCNAUGHTONSMITH, G A

AU - TAYLOR, R J K

PY - 1993/11/7

Y1 - 1993/11/7

N2 - The title reaction has been used to prepare nine-membered lactones commencing from 2-vinyltetrahydrofurans and dichloroketene; the resulting DELTA5-dichlorolactones are exclusively trans but dechlorination using Bu3SnH-AIBN (azoisobutyronitrile) achieves concomitant isomerisation to give the cis-unsaturated lactones.

AB - The title reaction has been used to prepare nine-membered lactones commencing from 2-vinyltetrahydrofurans and dichloroketene; the resulting DELTA5-dichlorolactones are exclusively trans but dechlorination using Bu3SnH-AIBN (azoisobutyronitrile) achieves concomitant isomerisation to give the cis-unsaturated lactones.

KW - HALICHONDRIA-OKADAI KADOTA

KW - PRELIMINARY COMMUNICATION

KW - ORGANOMETALLIC REAGENTS

KW - MACROLIDE ANTIBIOTICS

KW - MACROCYCLIC LACTONES

KW - NEOHALICHOLACTONE

KW - OBTUSENYNE

M3 - Article

SN - 0022-4936

SP - 1593

EP - 1595

JO - JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS

JF - JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS

IS - 21

ER -