Asymmetric total synthesis of (-)-merrilactone A: Use of a bulky protecting group as long-range stereocontrolling element

Masayuki Inoue, Takaaki Satou, Masahiro Hirama

Research output: Contribution to journalArticle

61 Citations (Scopus)

Abstract

(Chemical Equation Presented) Designer elegance: The transannular aldol reaction of a cyclooctene diketone is the key step in this total synthesis of the natural enantiomer of merrilactone A (see scheme). The configuration of the two stereocenters generated in the formation of the central bicyclo[3.3.0]octane framework of the natural product was established using a specially designed bulky protecting group.

Original languageEnglish
Pages (from-to)4843-4848
Number of pages6
JournalAngewandte Chemie - International Edition
Volume45
Issue number29
DOIs
Publication statusPublished - 2006 Jul 17
Externally publishedYes

Fingerprint

Enantiomers
Biological Products
octane
merrilactone A
3-hydroxybutanal

Keywords

  • Aldol reaction
  • Asymmetric synthesis
  • Medium-ring compounds
  • Protecting groups
  • Terpenoids

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Asymmetric total synthesis of (-)-merrilactone A : Use of a bulky protecting group as long-range stereocontrolling element. / Inoue, Masayuki; Satou, Takaaki; Hirama, Masahiro.

In: Angewandte Chemie - International Edition, Vol. 45, No. 29, 17.07.2006, p. 4843-4848.

Research output: Contribution to journalArticle

@article{3082ea17af3d4b498af28adcd2ce620d,
title = "Asymmetric total synthesis of (-)-merrilactone A: Use of a bulky protecting group as long-range stereocontrolling element",
abstract = "(Chemical Equation Presented) Designer elegance: The transannular aldol reaction of a cyclooctene diketone is the key step in this total synthesis of the natural enantiomer of merrilactone A (see scheme). The configuration of the two stereocenters generated in the formation of the central bicyclo[3.3.0]octane framework of the natural product was established using a specially designed bulky protecting group.",
keywords = "Aldol reaction, Asymmetric synthesis, Medium-ring compounds, Protecting groups, Terpenoids",
author = "Masayuki Inoue and Takaaki Satou and Masahiro Hirama",
year = "2006",
month = "7",
day = "17",
doi = "10.1002/anie.200601358",
language = "English",
volume = "45",
pages = "4843--4848",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "29",

}

TY - JOUR

T1 - Asymmetric total synthesis of (-)-merrilactone A

T2 - Use of a bulky protecting group as long-range stereocontrolling element

AU - Inoue, Masayuki

AU - Satou, Takaaki

AU - Hirama, Masahiro

PY - 2006/7/17

Y1 - 2006/7/17

N2 - (Chemical Equation Presented) Designer elegance: The transannular aldol reaction of a cyclooctene diketone is the key step in this total synthesis of the natural enantiomer of merrilactone A (see scheme). The configuration of the two stereocenters generated in the formation of the central bicyclo[3.3.0]octane framework of the natural product was established using a specially designed bulky protecting group.

AB - (Chemical Equation Presented) Designer elegance: The transannular aldol reaction of a cyclooctene diketone is the key step in this total synthesis of the natural enantiomer of merrilactone A (see scheme). The configuration of the two stereocenters generated in the formation of the central bicyclo[3.3.0]octane framework of the natural product was established using a specially designed bulky protecting group.

KW - Aldol reaction

KW - Asymmetric synthesis

KW - Medium-ring compounds

KW - Protecting groups

KW - Terpenoids

UR - http://www.scopus.com/inward/record.url?scp=33746787198&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33746787198&partnerID=8YFLogxK

U2 - 10.1002/anie.200601358

DO - 10.1002/anie.200601358

M3 - Article

C2 - 16795104

AN - SCOPUS:33746787198

VL - 45

SP - 4843

EP - 4848

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 29

ER -