Nucleophilic addition to n-allyl molybdenum complexes : a synthesis of the C1-C9 fragment of salinomycin
Nucleophilic addition to n-allyl molybdenum complexes : a synthesis of the C1-C9 fragment of salinomycin
The asymmetric synthesis of the C1-C9 fragment 1.5.1 of salinomycin was achieved in eighteen steps using three key transformations:-
(a) Sharpless asymmetric epoxidation to introduce the first chiral centres at C2 and C3.
(b) 1,4-Asymmetric induction to create the chiral centre at C6 in a thermodynamically controlled intramolecular cyclisation.
(c) Reductive lithiation followed by nucleophilic addition to a chiral π-allyl molybdenum complex 5.8.4 to control the configuration at C7 and C8.
The nucleophilic addition to the homochiral α-alkoxyanions derived from stannes 6.1.4 and 6.1.5 to chiral π-allyl molybdenum complexes to simultaneously create two adjacent stereogenic centres was studied. The results showed that a high degree of diastereo- and regio- control was possible using chiral complex 5.8.4. (Fig 13235a)
University of Southampton
1996
Procter, Martin James
(1996)
Nucleophilic addition to n-allyl molybdenum complexes : a synthesis of the C1-C9 fragment of salinomycin.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
The asymmetric synthesis of the C1-C9 fragment 1.5.1 of salinomycin was achieved in eighteen steps using three key transformations:-
(a) Sharpless asymmetric epoxidation to introduce the first chiral centres at C2 and C3.
(b) 1,4-Asymmetric induction to create the chiral centre at C6 in a thermodynamically controlled intramolecular cyclisation.
(c) Reductive lithiation followed by nucleophilic addition to a chiral π-allyl molybdenum complex 5.8.4 to control the configuration at C7 and C8.
The nucleophilic addition to the homochiral α-alkoxyanions derived from stannes 6.1.4 and 6.1.5 to chiral π-allyl molybdenum complexes to simultaneously create two adjacent stereogenic centres was studied. The results showed that a high degree of diastereo- and regio- control was possible using chiral complex 5.8.4. (Fig 13235a)
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Published date: 1996
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Local EPrints ID: 460180
URI: http://eprints.soton.ac.uk/id/eprint/460180
PURE UUID: 48bc0fa6-f388-461f-a16d-ce70f38d0b0f
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Date deposited: 04 Jul 2022 18:06
Last modified: 04 Jul 2022 18:06
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Author:
Martin James Procter
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