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
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
(2017)Doi:10.1055/s-1999-2765
(1999)Doi:10.1002/recl.19881070607
(1988)Doi:10.1016/S0957-4166(99)00151-2
(1999)Doi:10.1016/S1386-1425(01)00727-2
(2002)
