Tetrahedron Letters p. 2409 - 2412 (1987)
Update date:2022-07-30
Topics: NMR spectroscopy Chiral center Stereochemistry Total synthesis Lactone Reaction Optimization Stereochemical analysis Stereocontrolled Macrocyclic lactone Aspicilin
Waanders, P.P.
Thijs, L.
Zwanenburg, B.
The essential features of the enantiocontrolled total synthesis of (-)-aspicilin are the strategic use of the photochemical rearrangement of α,β-epoxy diazomethyl ketones to 4-hydroxyalkenoates (Scheme 1) and the stereochemical control of the Sharpless epoxidation, α,ο functionalization of an alkynol using potassium 3-aminopropylamine (KAPA) as acetylene zipper, coupling between C7 and C8 by means of a Wittig reaction and lactonization by using 2,6-dichlorobenzoyl chloride.
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Doi:10.1055/s-1987-28094
(1987)Doi:10.1002/anie.201610462
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