New Synthetic Technology for the Mild and Selective One-Carbon Homologation of Hindered Aldehydes in the Presence of Ketones

KC Nicolaou; G Vassilikogiannakis; R Kranich; PS Baran; YL Zhong; S Natarajan

doi:10.1021/ol000102u

New Synthetic Technology for the Mild and Selective One-Carbon Homologation of Hindered Aldehydes in the Presence of Ketones

Org Lett. 2000 Jun 29;2(13):1895-1898. doi: 10.1021/ol000102u.

Authors

KC Nicolaou¹, G Vassilikogiannakis, R Kranich, PS Baran, YL Zhong, S Natarajan

Affiliation

¹ Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, and Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093.

PMID: 10891185
DOI: 10.1021/ol000102u

Abstract

A selective, mild, and highly efficient method has been uncovered during the total synthesis of the CP molecules to accomplish the one-carbon homologation of sterically hindered aldehydes in the presence of acid- and base-labile moieties, Michael acceptors, and even other carbonyl groups such as reactive and epimerizable ketones. Mechanistic studies have revealed a neutral reagent for the rapid collapse of cyanohydrins to ketones.