Intramolecular cycloaddition/cycloreversion of (E)-3 beta,17 beta-diacetoxy-5,10-secoandrost-1(10)-en-5-one

V.A. Khripach; V.N. Zhabinskii; A.I. Kuchto; Y.Y. Zhiburtovich; V.V. Gromak; M.B. Groen; J. van der Louw; Æ. de Groot

doi:10.1016/j.tetlet.2006.07.096

Intramolecular cycloaddition/cycloreversion of (E)-3 beta,17 beta-diacetoxy-5,10-secoandrost-1(10)-en-5-one

V.A. Khripach, V.N. Zhabinskii, A.I. Kuchto, Y.Y. Zhiburtovich, V.V. Gromak, M.B. Groen, J. van der Louw, Æ. de Groot

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

18 Citations (Scopus)

Abstract

Treatment of 3 beta,17 beta-diacetoxy-5,10-secoandrost-1(10)-en-5-one with (BF3Et2O)-Et-. was shown to proceed with cleavage of the macrocycle and formation of a new compound containing a cyclopentenone ring. Based on DFT calculations, an intramolecular Lewis acid promoted [2+2]cycloaddition, followed by a cycloreversion of the intermediate oxetane, is proposed as a possible reaction mechanism.

Original language	English
Pages (from-to)	6715-6718
Journal	Tetrahedron Letters
Volume	47
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2006.07.096
Publication status	Published - 2006

Keywords

medium-sized ring
secosteroids
reactivity
steroids
nmr
program

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10.1016/j.tetlet.2006.07.096

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title = "Intramolecular cycloaddition/cycloreversion of (E)-3 beta,17 beta-diacetoxy-5,10-secoandrost-1(10)-en-5-one",

abstract = "Treatment of 3 beta,17 beta-diacetoxy-5,10-secoandrost-1(10)-en-5-one with (BF3Et2O)-Et-. was shown to proceed with cleavage of the macrocycle and formation of a new compound containing a cyclopentenone ring. Based on DFT calculations, an intramolecular Lewis acid promoted [2+2]cycloaddition, followed by a cycloreversion of the intermediate oxetane, is proposed as a possible reaction mechanism.",

keywords = "medium-sized ring, secosteroids, reactivity, steroids, nmr, program",

author = "V.A. Khripach and V.N. Zhabinskii and A.I. Kuchto and Y.Y. Zhiburtovich and V.V. Gromak and M.B. Groen and {van der Louw}, J. and {de Groot}, {\AE}.",

note = "ISI Document Delivery No.: 086JY Times Cited: 0 Cited Reference Count: 16",

year = "2006",

doi = "10.1016/j.tetlet.2006.07.096",

language = "English",

volume = "47",

pages = "6715--6718",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "38",

}

TY - JOUR

T1 - Intramolecular cycloaddition/cycloreversion of (E)-3 beta,17 beta-diacetoxy-5,10-secoandrost-1(10)-en-5-one

AU - Khripach, V.A.

AU - Zhabinskii, V.N.

AU - Kuchto, A.I.

AU - Zhiburtovich, Y.Y.

AU - Gromak, V.V.

AU - Groen, M.B.

AU - van der Louw, J.

AU - de Groot, Æ.

N1 - ISI Document Delivery No.: 086JY Times Cited: 0 Cited Reference Count: 16

PY - 2006

Y1 - 2006

N2 - Treatment of 3 beta,17 beta-diacetoxy-5,10-secoandrost-1(10)-en-5-one with (BF3Et2O)-Et-. was shown to proceed with cleavage of the macrocycle and formation of a new compound containing a cyclopentenone ring. Based on DFT calculations, an intramolecular Lewis acid promoted [2+2]cycloaddition, followed by a cycloreversion of the intermediate oxetane, is proposed as a possible reaction mechanism.

AB - Treatment of 3 beta,17 beta-diacetoxy-5,10-secoandrost-1(10)-en-5-one with (BF3Et2O)-Et-. was shown to proceed with cleavage of the macrocycle and formation of a new compound containing a cyclopentenone ring. Based on DFT calculations, an intramolecular Lewis acid promoted [2+2]cycloaddition, followed by a cycloreversion of the intermediate oxetane, is proposed as a possible reaction mechanism.

KW - medium-sized ring

KW - secosteroids

KW - reactivity

KW - steroids

KW - nmr

KW - program

U2 - 10.1016/j.tetlet.2006.07.096

DO - 10.1016/j.tetlet.2006.07.096

M3 - Article

SN - 0040-4039

VL - 47

SP - 6715

EP - 6718

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

Intramolecular cycloaddition/cycloreversion of (E)-3 beta,17 beta-diacetoxy-5,10-secoandrost-1(10)-en-5-one

Abstract

Keywords

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