Access to Wieland–Miescher Diketone-Derived Building Blocks by Stereoselective Construction of the C-9 Quaternary Carbon Center Using the Mukaiyama Aldol Reaction
The Mukaiyama aldol reaction has been used to efficiently install a lateral chain at the C-9 position of the Wieland–Miescher ketone derivative 3 within two steps, representing a shortcut compared to that of the classical sequences. The treatment of the silylated enol ether 8 with a wide range of acetals in the presence of tin tetrachloride led to a the diastereoselective construction of the C-9 quaternary
Synthesis of functionalized hydroxyphthalides and their conversion to 3-cyano-1(3H)-isobenzofuranones. The Diels-Alder reaction of methyl 4,4-diethoxybutynoate and cyclohexadienes
作者:John N. Freskos、Gary W. Morrow、John S. Swenton
DOI:10.1021/jo00206a016
日期:1985.3
Photolabile Protection of 1,2- and 1,3-Diols with Salicylaldehyde Derivatives
作者:Alexey P. Kostikov、Vladimir V. Popik
DOI:10.1021/ol802141g
日期:2008.11.20
1,2- and 1,3-diols, including carbohydrates, can be readily caged as acetals of 5-methoxy- or 5-hydroxysalicylaldehydes. Irradiation of these acetals with 300 nm light results in their efficient (Phi = 0.2-0.3) cleavage, regenerating an aldehyde and a glycol in excellent chemical yield. Photoreactive 5-hydroxysalicylaldehyde acetals can be produced by mild in situ reduction of photostable p-quinone precursors.
Direct Barbier-type allylation of aromatic acetals and dioxolanes in the presence of β-cyclodextrin in water
A new and convenient procedure for the synthesis of homoallylic alcohols directly from aromatic acetals and dioxolanes has been developed with very good yields under biomimetic conditions using a Zn-mediated Barbier-type allylation in the presence of beta-cyclodextrin in water. (c) 2006 Elsevier Ltd. All rights reserved.
Panek, James S.; Yang, Michael, Journal of the American Chemical Society, 1991, vol. 113, # 17, p. 6594 - 6600