Stereoselective total synthesis of nemorosone

Masahiro Uwamori; Aya Saito; Masahisa Nakada

doi:10.1021/jo300646j

Stereoselective total synthesis of nemorosone

Masahiro Uwamori, Aya Saito, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

54 Citations (Scopus)

Abstract

The highly stereoselective total synthesis of nemorosone via a new approach to the bicyclo[3.3.1]nonane-2,4,9-trione core which features intramolecular cyclopropanation of an α-diazo ketone, stereoselective alkylation at the C8 position, and regioselective ring-opening of cyclopropane is described. The total synthesis of nemorosone includes chemo- and stereoselective hydrogenation directed by the internal alkene.

Original language	English
Pages (from-to)	5098-5107
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	77
Issue number	11
DOIs	https://doi.org/10.1021/jo300646j
Publication status	Published - 2012 Jun 1

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo300646j

Cite this

@article{8ab9ecd8b7204533a99155d25a34ca08,

title = "Stereoselective total synthesis of nemorosone",

abstract = "The highly stereoselective total synthesis of nemorosone via a new approach to the bicyclo[3.3.1]nonane-2,4,9-trione core which features intramolecular cyclopropanation of an α-diazo ketone, stereoselective alkylation at the C8 position, and regioselective ring-opening of cyclopropane is described. The total synthesis of nemorosone includes chemo- and stereoselective hydrogenation directed by the internal alkene.",

author = "Masahiro Uwamori and Aya Saito and Masahisa Nakada",

year = "2012",

month = jun,

day = "1",

doi = "10.1021/jo300646j",

language = "English",

volume = "77",

pages = "5098--5107",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - Stereoselective total synthesis of nemorosone

AU - Uwamori, Masahiro

AU - Saito, Aya

AU - Nakada, Masahisa

PY - 2012/6/1

Y1 - 2012/6/1

N2 - The highly stereoselective total synthesis of nemorosone via a new approach to the bicyclo[3.3.1]nonane-2,4,9-trione core which features intramolecular cyclopropanation of an α-diazo ketone, stereoselective alkylation at the C8 position, and regioselective ring-opening of cyclopropane is described. The total synthesis of nemorosone includes chemo- and stereoselective hydrogenation directed by the internal alkene.

AB - The highly stereoselective total synthesis of nemorosone via a new approach to the bicyclo[3.3.1]nonane-2,4,9-trione core which features intramolecular cyclopropanation of an α-diazo ketone, stereoselective alkylation at the C8 position, and regioselective ring-opening of cyclopropane is described. The total synthesis of nemorosone includes chemo- and stereoselective hydrogenation directed by the internal alkene.

UR - http://www.scopus.com/inward/record.url?scp=84861798573&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84861798573&partnerID=8YFLogxK

U2 - 10.1021/jo300646j

DO - 10.1021/jo300646j

M3 - Article

C2 - 22563879

AN - SCOPUS:84861798573

SN - 0022-3263

VL - 77

SP - 5098

EP - 5107

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 11

ER -

Stereoselective total synthesis of nemorosone

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this