Hypervalent λ(n)-iodane-mediated fragmentation of tertiary cyclopropanol systems II: Application to asymmetric syntheses of piperidine and indolizidine alkaloids

Masayuki Kirihara; Takashi Nishio; Satoshi Yokoyama; Hiroko Kakuda; Takefumi Momose

doi:10.1016/S0040-4020(99)00073-3

Hypervalent λ(n)-iodane-mediated fragmentation of tertiary cyclopropanol systems II: Application to asymmetric syntheses of piperidine and indolizidine alkaloids

Masayuki Kirihara^*, Takashi Nishio, Satoshi Yokoyama, Hiroko Kakuda, Takefumi Momose

^*Corresponding author for this work

Faculty of Liberal Arts and Sciences

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

29 Scopus citations

Abstract

The asymmetric synthesis of (-)-pinidine and its enantiomer was accomplished by starting from norgranatanone via the asymmetric enolization, stereoselective cyclopropanation, and oxidative ring cleavage of the resulting cyclopropanol system with a hypervalent λ(n)-iodane as key steps. Formal asymmetric synthesis of (+)-indolizidine 223AB was also performed via the asymmetric enolization and oxidative ring cleavage of the resulting cyclopropanol system as key steps.

Original language	English
Pages (from-to)	2911-2926
Number of pages	16
Journal	Tetrahedron
Volume	55
Issue number	10
DOIs	https://doi.org/10.1016/S0040-4020(99)00073-3
State	Published - 1999/03/05

Keywords

Asymmetric synthesis
Cyclopropanes
Fragmentation reactions
Hypervalent elements

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(99)00073-3

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title = "Hypervalent λ(n)-iodane-mediated fragmentation of tertiary cyclopropanol systems II: Application to asymmetric syntheses of piperidine and indolizidine alkaloids",

abstract = "The asymmetric synthesis of (-)-pinidine and its enantiomer was accomplished by starting from norgranatanone via the asymmetric enolization, stereoselective cyclopropanation, and oxidative ring cleavage of the resulting cyclopropanol system with a hypervalent λ(n)-iodane as key steps. Formal asymmetric synthesis of (+)-indolizidine 223AB was also performed via the asymmetric enolization and oxidative ring cleavage of the resulting cyclopropanol system as key steps.",

keywords = "Asymmetric synthesis, Cyclopropanes, Fragmentation reactions, Hypervalent elements",

author = "Masayuki Kirihara and Takashi Nishio and Satoshi Yokoyama and Hiroko Kakuda and Takefumi Momose",

note = "Funding Information: This work was supported in part by Grants-in-Aid (No. 07772092 and No. 09672139) for Scientific Research from the Ministry of Education, Science, Sports and Culture, Japan.",

year = "1999",

month = mar,

day = "5",

doi = "10.1016/S0040-4020(99)00073-3",

language = "英語",

volume = "55",

pages = "2911--2926",

journal = "Tetrahedron",

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number = "10",

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TY - JOUR

T1 - Hypervalent λ(n)-iodane-mediated fragmentation of tertiary cyclopropanol systems II

T2 - Application to asymmetric syntheses of piperidine and indolizidine alkaloids

AU - Kirihara, Masayuki

AU - Nishio, Takashi

AU - Yokoyama, Satoshi

AU - Kakuda, Hiroko

AU - Momose, Takefumi

N1 - Funding Information: This work was supported in part by Grants-in-Aid (No. 07772092 and No. 09672139) for Scientific Research from the Ministry of Education, Science, Sports and Culture, Japan.

PY - 1999/3/5

Y1 - 1999/3/5

N2 - The asymmetric synthesis of (-)-pinidine and its enantiomer was accomplished by starting from norgranatanone via the asymmetric enolization, stereoselective cyclopropanation, and oxidative ring cleavage of the resulting cyclopropanol system with a hypervalent λ(n)-iodane as key steps. Formal asymmetric synthesis of (+)-indolizidine 223AB was also performed via the asymmetric enolization and oxidative ring cleavage of the resulting cyclopropanol system as key steps.

AB - The asymmetric synthesis of (-)-pinidine and its enantiomer was accomplished by starting from norgranatanone via the asymmetric enolization, stereoselective cyclopropanation, and oxidative ring cleavage of the resulting cyclopropanol system with a hypervalent λ(n)-iodane as key steps. Formal asymmetric synthesis of (+)-indolizidine 223AB was also performed via the asymmetric enolization and oxidative ring cleavage of the resulting cyclopropanol system as key steps.

KW - Asymmetric synthesis

KW - Cyclopropanes

KW - Fragmentation reactions

KW - Hypervalent elements

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U2 - 10.1016/S0040-4020(99)00073-3

DO - 10.1016/S0040-4020(99)00073-3

M3 - 学術論文

AN - SCOPUS:0033525637

SN - 0040-4020

VL - 55

SP - 2911

EP - 2926

JO - Tetrahedron

JF - Tetrahedron

IS - 10

ER -

Hypervalent λ(n)-iodane-mediated fragmentation of tertiary cyclopropanol systems II: Application to asymmetric syntheses of piperidine and indolizidine alkaloids

Abstract

Keywords

ASJC Scopus subject areas

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