Total synthesis of (+)- and (-)-sundiversifolide via intramolecular acylation and determination of the absolute configuration

Keiko Ohtsuki; Kazumasa Matsuo; Takashi Yoshikawa; Chihiro Moriya; Kaori Tomita-Yokotani; Kozo Shishido; Mitsuru Shindo

doi:10.1021/ol8001333

Total synthesis of (+)- and (-)-sundiversifolide via intramolecular acylation and determination of the absolute configuration

Keiko Ohtsuki, Kazumasa Matsuo, Takashi Yoshikawa, Chihiro Moriya, Kaori Tomita-Yokotani, Kozo Shishido, Mitsuru Shindo

Department of Fundamental Organic Chemistry

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

35 Citations (Scopus)

Abstract

Intramolecular acylation of an organolithium leads to an efficient stereocontrolled total synthesis of both enantiomers of sundiversifolide. The absolute configuration was determined by HPLC analysis and allelopathy assay. The y-lactone moiety resulted from a butenolide was obtained by the condensation of a bicyclic a-hydroxyhemiacetal with Ph₃P=CMe(CO₂R).

Original language	English
Pages (from-to)	1247-1250
Number of pages	4
Journal	Organic letters
Volume	10
Issue number	6
DOIs	https://doi.org/10.1021/ol8001333
Publication status	Published - Mar 20 2008

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol8001333

Cite this

@article{ae959ac3a8a143eb950e5b42ce294600,

title = "Total synthesis of (+)- and (-)-sundiversifolide via intramolecular acylation and determination of the absolute configuration",

abstract = "Intramolecular acylation of an organolithium leads to an efficient stereocontrolled total synthesis of both enantiomers of sundiversifolide. The absolute configuration was determined by HPLC analysis and allelopathy assay. The y-lactone moiety resulted from a butenolide was obtained by the condensation of a bicyclic a-hydroxyhemiacetal with Ph3P=CMe(CO2R).",

author = "Keiko Ohtsuki and Kazumasa Matsuo and Takashi Yoshikawa and Chihiro Moriya and Kaori Tomita-Yokotani and Kozo Shishido and Mitsuru Shindo",

year = "2008",

month = mar,

day = "20",

doi = "10.1021/ol8001333",

language = "English",

volume = "10",

pages = "1247--1250",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - Total synthesis of (+)- and (-)-sundiversifolide via intramolecular acylation and determination of the absolute configuration

AU - Ohtsuki, Keiko

AU - Matsuo, Kazumasa

AU - Yoshikawa, Takashi

AU - Moriya, Chihiro

AU - Tomita-Yokotani, Kaori

AU - Shishido, Kozo

AU - Shindo, Mitsuru

PY - 2008/3/20

Y1 - 2008/3/20

N2 - Intramolecular acylation of an organolithium leads to an efficient stereocontrolled total synthesis of both enantiomers of sundiversifolide. The absolute configuration was determined by HPLC analysis and allelopathy assay. The y-lactone moiety resulted from a butenolide was obtained by the condensation of a bicyclic a-hydroxyhemiacetal with Ph3P=CMe(CO2R).

AB - Intramolecular acylation of an organolithium leads to an efficient stereocontrolled total synthesis of both enantiomers of sundiversifolide. The absolute configuration was determined by HPLC analysis and allelopathy assay. The y-lactone moiety resulted from a butenolide was obtained by the condensation of a bicyclic a-hydroxyhemiacetal with Ph3P=CMe(CO2R).

UR - http://www.scopus.com/inward/record.url?scp=44249084506&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=44249084506&partnerID=8YFLogxK

U2 - 10.1021/ol8001333

DO - 10.1021/ol8001333

M3 - Article

C2 - 18288857

AN - SCOPUS:44249084506

SN - 1523-7060

VL - 10

SP - 1247

EP - 1250

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Total synthesis of (+)- and (-)-sundiversifolide via intramolecular acylation and determination of the absolute configuration

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this