Palladium (II) catalyzed regioselective lactonization of steroids. Chemoselective construction of novel estrone derivatives

L. Troisi; G. Vasapollo; B. El Ali; G. Mele; S. Florio; V. Capriati

doi:10.1016/S0040-4039(99)00094-5

Palladium (II) catalyzed regioselective lactonization of steroids. Chemoselective construction of novel estrone derivatives

L. Troisi, G. Vasapollo, B. El Ali, G. Mele, S. Florio, V. Capriati

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

31 Scopus citations

Abstract

Palladium acetate and 1,4-bis(diphenylphosphino)butane (dppb) catalyze regioselective cyclocarbonylation of 4-allylsteroids forming exclusively 7- membered ring lactones with excellent yields (96-98 %). The stereoselective addition of an epoxide ring on the side-chain of steroids is realized by coupling the carbonyl group of the cyclopentanone ring of the steroid with 2- benzothiazolylchloromethyllithium 1 or 4,4-dimethyl-2- oxazolinylchloroalkylithiums 2 and 3.

Original language	English
Pages (from-to)	1771-1774
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	9
DOIs	https://doi.org/10.1016/S0040-4039(99)00094-5
State	Published - 26 Feb 1999

Bibliographical note

Funding Information:
This study was supported by grants from the Swedish Cancer Society.

Keywords

Epoxides
Lactones
Palladium
Steroids

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)00094-5

Cite this

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title = "Palladium (II) catalyzed regioselective lactonization of steroids. Chemoselective construction of novel estrone derivatives",

abstract = "Palladium acetate and 1,4-bis(diphenylphosphino)butane (dppb) catalyze regioselective cyclocarbonylation of 4-allylsteroids forming exclusively 7- membered ring lactones with excellent yields (96-98 \%). The stereoselective addition of an epoxide ring on the side-chain of steroids is realized by coupling the carbonyl group of the cyclopentanone ring of the steroid with 2- benzothiazolylchloromethyllithium 1 or 4,4-dimethyl-2- oxazolinylchloroalkylithiums 2 and 3.",

keywords = "Epoxides, Lactones, Palladium, Steroids",

author = "L. Troisi and G. Vasapollo and \{El Ali\}, B. and G. Mele and S. Florio and V. Capriati",

note = "Funding Information: This study was supported by grants from the Swedish Cancer Society.",

year = "1999",

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day = "26",

doi = "10.1016/S0040-4039(99)00094-5",

language = "English",

volume = "40",

pages = "1771--1774",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Palladium (II) catalyzed regioselective lactonization of steroids. Chemoselective construction of novel estrone derivatives

AU - Troisi, L.

AU - Vasapollo, G.

AU - El Ali, B.

AU - Mele, G.

AU - Florio, S.

AU - Capriati, V.

N1 - Funding Information: This study was supported by grants from the Swedish Cancer Society.

PY - 1999/2/26

Y1 - 1999/2/26

N2 - Palladium acetate and 1,4-bis(diphenylphosphino)butane (dppb) catalyze regioselective cyclocarbonylation of 4-allylsteroids forming exclusively 7- membered ring lactones with excellent yields (96-98 %). The stereoselective addition of an epoxide ring on the side-chain of steroids is realized by coupling the carbonyl group of the cyclopentanone ring of the steroid with 2- benzothiazolylchloromethyllithium 1 or 4,4-dimethyl-2- oxazolinylchloroalkylithiums 2 and 3.

AB - Palladium acetate and 1,4-bis(diphenylphosphino)butane (dppb) catalyze regioselective cyclocarbonylation of 4-allylsteroids forming exclusively 7- membered ring lactones with excellent yields (96-98 %). The stereoselective addition of an epoxide ring on the side-chain of steroids is realized by coupling the carbonyl group of the cyclopentanone ring of the steroid with 2- benzothiazolylchloromethyllithium 1 or 4,4-dimethyl-2- oxazolinylchloroalkylithiums 2 and 3.

KW - Epoxides

KW - Lactones

KW - Palladium

KW - Steroids

UR - https://www.scopus.com/pages/publications/0033605407

U2 - 10.1016/S0040-4039(99)00094-5

DO - 10.1016/S0040-4039(99)00094-5

M3 - Article

AN - SCOPUS:0033605407

SN - 0040-4039

VL - 40

SP - 1771

EP - 1774

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 9

ER -

Palladium (II) catalyzed regioselective lactonization of steroids. Chemoselective construction of novel estrone derivatives

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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