Synthesis of terpene and steroid dimers and trimers having cyclobutadienyl-Co and aromatic tethers

Miguel A. Sierra; M. Rosario Torres; María C. De La Torre; Elsa Álvaro

doi:10.1021/jo0703698

Synthesis of terpene and steroid dimers and trimers having cyclobutadienyl-Co and aromatic tethers

Miguel A. Sierra^*, M. Rosario Torres, María C. De La Torre, Elsa Álvaro

^*Corresponding author for this work

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Abstract

(Chemical Equation Presented) The reaction of natural product derived propargylic alcohols with CpCo(CO)₂ produces three new types of natural product hybrids having two or three terpene or steroid fragments. The tether joining the natural product subunits is built during the reaction. Type 1 hybrids have two terpene or steroid moieties joined by a CpCo-cyclobutadiene tether, with the two units disposed in a 1,2-arrangement (9, 14, 22). Type 2 hybrids have a Co-cyclopentadienone tether (10). Type 3 has three units of terpene or steroid joined to a benzene ring (11, 12, 15). An unusual Co-mediated β-carbon elimination pathway of propargylic alcohols leading to ketones (an unknown process in this chemistry) has been observed.

Original language	English (US)
Pages (from-to)	4213-4219
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	72
Issue number	11
DOIs	https://doi.org/10.1021/jo0703698
State	Published - May 25 2007

ASJC Scopus subject areas

Organic Chemistry

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title = "Synthesis of terpene and steroid dimers and trimers having cyclobutadienyl-Co and aromatic tethers",

abstract = "(Chemical Equation Presented) The reaction of natural product derived propargylic alcohols with CpCo(CO)2 produces three new types of natural product hybrids having two or three terpene or steroid fragments. The tether joining the natural product subunits is built during the reaction. Type 1 hybrids have two terpene or steroid moieties joined by a CpCo-cyclobutadiene tether, with the two units disposed in a 1,2-arrangement (9, 14, 22). Type 2 hybrids have a Co-cyclopentadienone tether (10). Type 3 has three units of terpene or steroid joined to a benzene ring (11, 12, 15). An unusual Co-mediated β-carbon elimination pathway of propargylic alcohols leading to ketones (an unknown process in this chemistry) has been observed.",

author = "Sierra, {Miguel A.} and Torres, {M. Rosario} and {De La Torre}, {Mar{\'i}a C.} and Elsa {\'A}lvaro",

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doi = "10.1021/jo0703698",

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TY - JOUR

T1 - Synthesis of terpene and steroid dimers and trimers having cyclobutadienyl-Co and aromatic tethers

AU - Sierra, Miguel A.

AU - Torres, M. Rosario

AU - De La Torre, María C.

AU - Álvaro, Elsa

PY - 2007/5/25

Y1 - 2007/5/25

N2 - (Chemical Equation Presented) The reaction of natural product derived propargylic alcohols with CpCo(CO)2 produces three new types of natural product hybrids having two or three terpene or steroid fragments. The tether joining the natural product subunits is built during the reaction. Type 1 hybrids have two terpene or steroid moieties joined by a CpCo-cyclobutadiene tether, with the two units disposed in a 1,2-arrangement (9, 14, 22). Type 2 hybrids have a Co-cyclopentadienone tether (10). Type 3 has three units of terpene or steroid joined to a benzene ring (11, 12, 15). An unusual Co-mediated β-carbon elimination pathway of propargylic alcohols leading to ketones (an unknown process in this chemistry) has been observed.

AB - (Chemical Equation Presented) The reaction of natural product derived propargylic alcohols with CpCo(CO)2 produces three new types of natural product hybrids having two or three terpene or steroid fragments. The tether joining the natural product subunits is built during the reaction. Type 1 hybrids have two terpene or steroid moieties joined by a CpCo-cyclobutadiene tether, with the two units disposed in a 1,2-arrangement (9, 14, 22). Type 2 hybrids have a Co-cyclopentadienone tether (10). Type 3 has three units of terpene or steroid joined to a benzene ring (11, 12, 15). An unusual Co-mediated β-carbon elimination pathway of propargylic alcohols leading to ketones (an unknown process in this chemistry) has been observed.

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Synthesis of terpene and steroid dimers and trimers having cyclobutadienyl-Co and aromatic tethers

Abstract

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