Highly efficient total synthesis of (+)-citreoviral

Yoshihisa Murata, Tomoyuki Kamino, Toshiaki Aoki, Seijiro Hosokawa, Susumu Kobayashi

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Only eight steps were required for the total synthesis of (+)-citreoviral (3) from chiral imide 1 in 18% overall yield. The key steps included a highly anti-selective aldol reaction, the stereoselective iodolactonization of a γ,δ-unsaturated β-hydroxyimide, and an intramolecular S N2 reaction of a tertiary alcohol to form intermediate 2.

Original languageEnglish
Pages (from-to)3175-3177
Number of pages3
JournalAngewandte Chemie - International Edition
Volume43
Issue number24
DOIs
Publication statusPublished - 2004 Jun 14
Externally publishedYes

Fingerprint

Imides
Alcohols
citreoviral
3-hydroxybutanal

Keywords

  • Alcohols
  • Aldol reaction
  • Lactones
  • Natural products
  • Total synthesis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Highly efficient total synthesis of (+)-citreoviral. / Murata, Yoshihisa; Kamino, Tomoyuki; Aoki, Toshiaki; Hosokawa, Seijiro; Kobayashi, Susumu.

In: Angewandte Chemie - International Edition, Vol. 43, No. 24, 14.06.2004, p. 3175-3177.

Research output: Contribution to journalArticle

Murata, Yoshihisa ; Kamino, Tomoyuki ; Aoki, Toshiaki ; Hosokawa, Seijiro ; Kobayashi, Susumu. / Highly efficient total synthesis of (+)-citreoviral. In: Angewandte Chemie - International Edition. 2004 ; Vol. 43, No. 24. pp. 3175-3177.
@article{9c08115ca3b446ecb093a3f825d6ea3c,
title = "Highly efficient total synthesis of (+)-citreoviral",
abstract = "Only eight steps were required for the total synthesis of (+)-citreoviral (3) from chiral imide 1 in 18{\%} overall yield. The key steps included a highly anti-selective aldol reaction, the stereoselective iodolactonization of a γ,δ-unsaturated β-hydroxyimide, and an intramolecular S N2 reaction of a tertiary alcohol to form intermediate 2.",
keywords = "Alcohols, Aldol reaction, Lactones, Natural products, Total synthesis",
author = "Yoshihisa Murata and Tomoyuki Kamino and Toshiaki Aoki and Seijiro Hosokawa and Susumu Kobayashi",
year = "2004",
month = "6",
day = "14",
doi = "10.1002/anie.200454212",
language = "English",
volume = "43",
pages = "3175--3177",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "24",

}

TY - JOUR

T1 - Highly efficient total synthesis of (+)-citreoviral

AU - Murata, Yoshihisa

AU - Kamino, Tomoyuki

AU - Aoki, Toshiaki

AU - Hosokawa, Seijiro

AU - Kobayashi, Susumu

PY - 2004/6/14

Y1 - 2004/6/14

N2 - Only eight steps were required for the total synthesis of (+)-citreoviral (3) from chiral imide 1 in 18% overall yield. The key steps included a highly anti-selective aldol reaction, the stereoselective iodolactonization of a γ,δ-unsaturated β-hydroxyimide, and an intramolecular S N2 reaction of a tertiary alcohol to form intermediate 2.

AB - Only eight steps were required for the total synthesis of (+)-citreoviral (3) from chiral imide 1 in 18% overall yield. The key steps included a highly anti-selective aldol reaction, the stereoselective iodolactonization of a γ,δ-unsaturated β-hydroxyimide, and an intramolecular S N2 reaction of a tertiary alcohol to form intermediate 2.

KW - Alcohols

KW - Aldol reaction

KW - Lactones

KW - Natural products

KW - Total synthesis

UR - http://www.scopus.com/inward/record.url?scp=4544311529&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=4544311529&partnerID=8YFLogxK

U2 - 10.1002/anie.200454212

DO - 10.1002/anie.200454212

M3 - Article

VL - 43

SP - 3175

EP - 3177

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 24

ER -