Enantioselective total synthesis of (-)-FR182877

Natsumi Tanaka Suzuki; Takahiro Suzuki; Takehiko Matsumura; Yousuke Hosoya; Tomoyuki Nakazato; Masahisa Nakada

doi:10.5059/yukigoseikyokaishi.69.646

Enantioselective total synthesis of (-)-FR182877

Natsumi Tanaka Suzuki^*, Takahiro Suzuki, Takehiko Matsumura, Yousuke Hosoya, Tomoyuki Nakazato, Masahisa Nakada

^*Corresponding author for this work

School of Advanced Science and Engineering

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

1 Citation (Scopus)

Abstract

An enantioselective total syntfiesis of (-)-FR182877 is described. This total synthesis features 1) the one-pot stereoselective tandem IMDA-IMHDA reaction which affords the tetracyclic compound including the ABCD ring system of (-)-FR182877 with the correct new seven stereogenie centers, 2) the palladium-mediated 7-exo-trig intramolecular Heck reaction for the construction of the highly strained seven-membefed F-ring, and 3) the iridium-mediated isomerization of the allylic alcohol to the a-methyl ketone followed by epimerization and the stereoselective reduction to furnish all the stereogenic centers of (-)-FR182877.

Original language	English
Pages (from-to)	646-660
Number of pages	15
Journal	Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume	69
Issue number	6
DOIs	https://doi.org/10.5059/yukigoseikyokaishi.69.646
Publication status	Published - 2011 Jun 1

Keywords

Anti-tumor cell compound
Enantioselective total synthesis
Intramolecular Heck reaction
Intramolecular diels-alder (IMDA) reaction
Intramolecular hetero diels-alder (IMHDA) reaction
Isomerisation reaction
Strained compound
Tandem IMDA-IMHDA reaction

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.5059/yukigoseikyokaishi.69.646

Cite this

@article{60b99213cdbd45dc9c6902f01cdbc6a9,

title = "Enantioselective total synthesis of (-)-FR182877",

abstract = "An enantioselective total syntfiesis of (-)-FR182877 is described. This total synthesis features 1) the one-pot stereoselective tandem IMDA-IMHDA reaction which affords the tetracyclic compound including the ABCD ring system of (-)-FR182877 with the correct new seven stereogenie centers, 2) the palladium-mediated 7-exo-trig intramolecular Heck reaction for the construction of the highly strained seven-membefed F-ring, and 3) the iridium-mediated isomerization of the allylic alcohol to the a-methyl ketone followed by epimerization and the stereoselective reduction to furnish all the stereogenic centers of (-)-FR182877.",

keywords = "Anti-tumor cell compound, Enantioselective total synthesis, Intramolecular Heck reaction, Intramolecular diels-alder (IMDA) reaction, Intramolecular hetero diels-alder (IMHDA) reaction, Isomerisation reaction, Strained compound, Tandem IMDA-IMHDA reaction",

author = "Suzuki, {Natsumi Tanaka} and Takahiro Suzuki and Takehiko Matsumura and Yousuke Hosoya and Tomoyuki Nakazato and Masahisa Nakada",

year = "2011",

month = jun,

day = "1",

doi = "10.5059/yukigoseikyokaishi.69.646",

language = "English",

volume = "69",

pages = "646--660",

journal = "Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry",

issn = "0037-9980",

publisher = "Society of Synthetic Organic Chemistry",

number = "6",

}

TY - JOUR

T1 - Enantioselective total synthesis of (-)-FR182877

AU - Suzuki, Natsumi Tanaka

AU - Suzuki, Takahiro

AU - Matsumura, Takehiko

AU - Hosoya, Yousuke

AU - Nakazato, Tomoyuki

AU - Nakada, Masahisa

PY - 2011/6/1

Y1 - 2011/6/1

N2 - An enantioselective total syntfiesis of (-)-FR182877 is described. This total synthesis features 1) the one-pot stereoselective tandem IMDA-IMHDA reaction which affords the tetracyclic compound including the ABCD ring system of (-)-FR182877 with the correct new seven stereogenie centers, 2) the palladium-mediated 7-exo-trig intramolecular Heck reaction for the construction of the highly strained seven-membefed F-ring, and 3) the iridium-mediated isomerization of the allylic alcohol to the a-methyl ketone followed by epimerization and the stereoselective reduction to furnish all the stereogenic centers of (-)-FR182877.

AB - An enantioselective total syntfiesis of (-)-FR182877 is described. This total synthesis features 1) the one-pot stereoselective tandem IMDA-IMHDA reaction which affords the tetracyclic compound including the ABCD ring system of (-)-FR182877 with the correct new seven stereogenie centers, 2) the palladium-mediated 7-exo-trig intramolecular Heck reaction for the construction of the highly strained seven-membefed F-ring, and 3) the iridium-mediated isomerization of the allylic alcohol to the a-methyl ketone followed by epimerization and the stereoselective reduction to furnish all the stereogenic centers of (-)-FR182877.

KW - Anti-tumor cell compound

KW - Enantioselective total synthesis

KW - Intramolecular Heck reaction

KW - Intramolecular diels-alder (IMDA) reaction

KW - Intramolecular hetero diels-alder (IMHDA) reaction

KW - Isomerisation reaction

KW - Strained compound

KW - Tandem IMDA-IMHDA reaction

UR - http://www.scopus.com/inward/record.url?scp=80053929691&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80053929691&partnerID=8YFLogxK

U2 - 10.5059/yukigoseikyokaishi.69.646

DO - 10.5059/yukigoseikyokaishi.69.646

M3 - Article

AN - SCOPUS:80053929691

SN - 0037-9980

VL - 69

SP - 646

EP - 660

JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

IS - 6

ER -

Enantioselective total synthesis of (-)-FR182877

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this