TOTAL SYNTHESIS of (+)-MONOMORINE I VIA ASYMMETRIC a-KETONIC CLEAVAGE of 8-AZABICYCLO[3: 2.1]0CTAN-3-ONE

Takefumi Momose; Naoki Toyooka; Sumie Seki; Yoshiro Hirai

doi:10.1248/cpb.38.2072

TOTAL SYNTHESIS of (+)-MONOMORINE I VIA ASYMMETRIC a-KETONIC CLEAVAGE of 8-AZABICYCLO[3: 2.1]0CTAN-3-ONE

Takefumi Momose, Naoki Toyooka, Sumie Seki, Yoshiro Hirai

Life Sciences and Bioengineering

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

44 Scopus citations

Abstract

The total synthesis of (+)-monomorine I and preparation of c/.y-2,5-difunctionalized pyrrolidines, as a chiral synthon, starting with asymmetric cleavage of the ' fork head’ ketone of 8-azabicyclo[3.2.1]octan-3-one are described.

Original language	English
Pages (from-to)	2072-2074
Number of pages	3
Journal	Chemical and Pharmaceutical Bulletin
Volume	38
Issue number	7
DOIs	https://doi.org/10.1248/cpb.38.2072
State	Published - 1990

Keywords

(+)-monomorine I
8-azabicyclo[3.2.1]octan-3-one
ant pheromone a-symmetric pyrrolidine
asymmetric deprotonation
asymmetric α-ketonic cleavage
ozonolysis
α-symmetric bicyclic ketone
α-symmetric pyrrolidine
‘fork head’ ketone

ASJC Scopus subject areas

General Chemistry
Drug Discovery

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@article{a6a3821b76c44056ac5d89e6c95e3b88,

title = "TOTAL SYNTHESIS of (+)-MONOMORINE I VIA ASYMMETRIC a-KETONIC CLEAVAGE of 8-AZABICYCLO[3: 2.1]0CTAN-3-ONE",

abstract = "The total synthesis of (+)-monomorine I and preparation of c/.y-2,5-difunctionalized pyrrolidines, as a chiral synthon, starting with asymmetric cleavage of the ' fork head{\textquoteright} ketone of 8-azabicyclo[3.2.1]octan-3-one are described.",

keywords = "(+)-monomorine I, 8-azabicyclo[3.2.1]octan-3-one, ant pheromone a-symmetric pyrrolidine, asymmetric deprotonation, asymmetric α-ketonic cleavage, ozonolysis, α-symmetric bicyclic ketone, α-symmetric pyrrolidine, {\textquoteleft}fork head{\textquoteright} ketone",

author = "Takefumi Momose and Naoki Toyooka and Sumie Seki and Yoshiro Hirai",

year = "1990",

doi = "10.1248/cpb.38.2072",

language = "英語",

volume = "38",

pages = "2072--2074",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "7",

}

TY - JOUR

T1 - TOTAL SYNTHESIS of (+)-MONOMORINE I VIA ASYMMETRIC a-KETONIC CLEAVAGE of 8-AZABICYCLO[3

T2 - 2.1]0CTAN-3-ONE

AU - Momose, Takefumi

AU - Toyooka, Naoki

AU - Seki, Sumie

AU - Hirai, Yoshiro

PY - 1990

Y1 - 1990

N2 - The total synthesis of (+)-monomorine I and preparation of c/.y-2,5-difunctionalized pyrrolidines, as a chiral synthon, starting with asymmetric cleavage of the ' fork head’ ketone of 8-azabicyclo[3.2.1]octan-3-one are described.

AB - The total synthesis of (+)-monomorine I and preparation of c/.y-2,5-difunctionalized pyrrolidines, as a chiral synthon, starting with asymmetric cleavage of the ' fork head’ ketone of 8-azabicyclo[3.2.1]octan-3-one are described.

KW - (+)-monomorine I

KW - 8-azabicyclo[3.2.1]octan-3-one

KW - ant pheromone a-symmetric pyrrolidine

KW - asymmetric deprotonation

KW - asymmetric α-ketonic cleavage

KW - ozonolysis

KW - α-symmetric bicyclic ketone

KW - α-symmetric pyrrolidine

KW - ‘fork head’ ketone

UR - http://www.scopus.com/inward/record.url?scp=0025041475&partnerID=8YFLogxK

U2 - 10.1248/cpb.38.2072

DO - 10.1248/cpb.38.2072

M3 - 学術論文

AN - SCOPUS:0025041475

SN - 0009-2363

VL - 38

SP - 2072

EP - 2074

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 7

ER -

TOTAL SYNTHESIS of (+)-MONOMORINE I VIA ASYMMETRIC a-KETONIC CLEAVAGE of 8-AZABICYCLO[3: 2.1]0CTAN-3-ONE

Abstract

Keywords

ASJC Scopus subject areas

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