New route to the synthesis of the illudane skeleton by Michael-Michael- elimination reaction

Kazuo Tokuzaki; Yasuhiro Kanemitu; Takehiko Yoshimitsu; Hiroto Nagaoka

doi:10.1016/S0040-4039(00)00974-6

New route to the synthesis of the illudane skeleton by Michael-Michael- elimination reaction

Kazuo Tokuzaki, Yasuhiro Kanemitu, Takehiko Yoshimitsu, Hiroto Nagaoka

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

12 Citations (Scopus)

Abstract

A new route to the synthesis of an optically active illudane skeleton from (R)-(-)-pantolactone (4) is established. The tricyclic ring system was constructed by Michael-Michael-elimination reaction of the enolate of (3S,5R)-3-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-1- propionylcyclopentene (10) with ethyl cyclopropylidenacetate (3).

Original language	English
Pages (from-to)	5923-5926
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	31
DOIs	https://doi.org/10.1016/S0040-4039(00)00974-6
Publication status	Published - Jul 29 2000
Externally published	Yes

Keywords

Antitumor compounds
Michael reactions
Terpenes and terpenoids

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(00)00974-6

Cite this

@article{8be478824c244740802c3011824cf3fd,

title = "New route to the synthesis of the illudane skeleton by Michael-Michael- elimination reaction",

abstract = "A new route to the synthesis of an optically active illudane skeleton from (R)-(-)-pantolactone (4) is established. The tricyclic ring system was constructed by Michael-Michael-elimination reaction of the enolate of (3S,5R)-3-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-1- propionylcyclopentene (10) with ethyl cyclopropylidenacetate (3).",

keywords = "Antitumor compounds, Michael reactions, Terpenes and terpenoids",

author = "Kazuo Tokuzaki and Yasuhiro Kanemitu and Takehiko Yoshimitsu and Hiroto Nagaoka",

year = "2000",

month = jul,

day = "29",

doi = "10.1016/S0040-4039(00)00974-6",

language = "English",

volume = "41",

pages = "5923--5926",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "31",

}

TY - JOUR

T1 - New route to the synthesis of the illudane skeleton by Michael-Michael- elimination reaction

AU - Tokuzaki, Kazuo

AU - Kanemitu, Yasuhiro

AU - Yoshimitsu, Takehiko

AU - Nagaoka, Hiroto

PY - 2000/7/29

Y1 - 2000/7/29

N2 - A new route to the synthesis of an optically active illudane skeleton from (R)-(-)-pantolactone (4) is established. The tricyclic ring system was constructed by Michael-Michael-elimination reaction of the enolate of (3S,5R)-3-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-1- propionylcyclopentene (10) with ethyl cyclopropylidenacetate (3).

AB - A new route to the synthesis of an optically active illudane skeleton from (R)-(-)-pantolactone (4) is established. The tricyclic ring system was constructed by Michael-Michael-elimination reaction of the enolate of (3S,5R)-3-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-1- propionylcyclopentene (10) with ethyl cyclopropylidenacetate (3).

KW - Antitumor compounds

KW - Michael reactions

KW - Terpenes and terpenoids

UR - http://www.scopus.com/inward/record.url?scp=0034729922&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034729922&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)00974-6

DO - 10.1016/S0040-4039(00)00974-6

M3 - Article

AN - SCOPUS:0034729922

SN - 0040-4039

VL - 41

SP - 5923

EP - 5926

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

New route to the synthesis of the illudane skeleton by Michael-Michael- elimination reaction

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this