Multistep Continuous-Flow Synthesis of (-)-Oseltamivir

Shin Ogasawara; Yujiro Hayashi

doi:10.1055/s-2016-0036-1588899

Multistep Continuous-Flow Synthesis of (-)-Oseltamivir

Shin Ogasawara, Yujiro Hayashi

SCI - Chemistry

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

21 Citations (Scopus)

Abstract

A continuous-flow synthesis of (-)-oseltamivir composed of five flow units was accomplished. In each unit, the following reactions proceed efficiently: (1) a diphenylprolinol silyl ether mediated Michael reaction, (2) a domino reaction of Michael and intermolecular Horner-Wadsworth-Emmons reactions, (3) protonation, (4) epimerization, and (5) reduction of a nitro group to an amine. (-)-Oseltamivir was obtained in 13% total yield through a single flow with a residence time of 310 minutes.

Original language	English
Article number	ss-2016-z0587-op
Pages (from-to)	424-428
Number of pages	5
Journal	Synthesis (Germany)
Volume	49
Issue number	2
DOIs	https://doi.org/10.1055/s-2016-0036-1588899
Publication status	Published - 2017 Jan 18

Keywords

Tamiflu
continuous flow
organocatalysis
time economy
total synthesis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1055/s-2016-0036-1588899

Fingerprint Dive into the research topics of 'Multistep Continuous-Flow Synthesis of (-)-Oseltamivir'. Together they form a unique fingerprint.

Cite this

@article{8db7d9b6cfcb4c1cb597ccf6989eeebb,

title = "Multistep Continuous-Flow Synthesis of (-)-Oseltamivir",

abstract = "A continuous-flow synthesis of (-)-oseltamivir composed of five flow units was accomplished. In each unit, the following reactions proceed efficiently: (1) a diphenylprolinol silyl ether mediated Michael reaction, (2) a domino reaction of Michael and intermolecular Horner-Wadsworth-Emmons reactions, (3) protonation, (4) epimerization, and (5) reduction of a nitro group to an amine. (-)-Oseltamivir was obtained in 13% total yield through a single flow with a residence time of 310 minutes.",

keywords = "Tamiflu, continuous flow, organocatalysis, time economy, total synthesis",

author = "Shin Ogasawara and Yujiro Hayashi",

year = "2017",

month = jan,

day = "18",

doi = "10.1055/s-2016-0036-1588899",

language = "English",

volume = "49",

pages = "424--428",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "2",

}

TY - JOUR

T1 - Multistep Continuous-Flow Synthesis of (-)-Oseltamivir

AU - Ogasawara, Shin

AU - Hayashi, Yujiro

PY - 2017/1/18

Y1 - 2017/1/18

N2 - A continuous-flow synthesis of (-)-oseltamivir composed of five flow units was accomplished. In each unit, the following reactions proceed efficiently: (1) a diphenylprolinol silyl ether mediated Michael reaction, (2) a domino reaction of Michael and intermolecular Horner-Wadsworth-Emmons reactions, (3) protonation, (4) epimerization, and (5) reduction of a nitro group to an amine. (-)-Oseltamivir was obtained in 13% total yield through a single flow with a residence time of 310 minutes.

AB - A continuous-flow synthesis of (-)-oseltamivir composed of five flow units was accomplished. In each unit, the following reactions proceed efficiently: (1) a diphenylprolinol silyl ether mediated Michael reaction, (2) a domino reaction of Michael and intermolecular Horner-Wadsworth-Emmons reactions, (3) protonation, (4) epimerization, and (5) reduction of a nitro group to an amine. (-)-Oseltamivir was obtained in 13% total yield through a single flow with a residence time of 310 minutes.

KW - Tamiflu

KW - continuous flow

KW - organocatalysis

KW - time economy

KW - total synthesis

UR - http://www.scopus.com/inward/record.url?scp=84994558901&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84994558901&partnerID=8YFLogxK

U2 - 10.1055/s-2016-0036-1588899

DO - 10.1055/s-2016-0036-1588899

M3 - Article

AN - SCOPUS:84994558901

VL - 49

SP - 424

EP - 428

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 2

M1 - ss-2016-z0587-op

ER -