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

Masayuki Inoue; Takaaki Sato; Masahiro Hirama

doi:10.1002/anie.200601358

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

Masayuki Inoue, Takaaki Sato, Masahiro Hirama

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

69 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 language	English
Pages (from-to)	4843-4848
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	29
DOIs	https://doi.org/10.1002/anie.200601358
Publication status	Published - 2006 Jul 17
Externally published	Yes

Keywords

Aldol reaction
Asymmetric synthesis
Medium-ring compounds
Protecting groups
Terpenoids

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1002/anie.200601358

Cite this

@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 Sato and Masahiro Hirama",

year = "2006",

month = jul,

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 - Sato, 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 -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this