Stereoselective synthesis of rapamycin fragment to build a macrocyclic toolbox

Shiva Krishna Reddy Guduru, Ravikumar Jimmidi, Girdhar Singh Deora, Prabhat Arya

Research output: Contribution to journalArticleOtherpeer-review

8 Citations (Scopus)

Abstract

A stereoselective synthesis of a rapamycin fragment is developed and further utilized toward building a macrocyclic chemical toolbox. The amino alcohol moiety embedded in the 22-membered macrocyclic ring allowed for the addition of a variation in the chiral side chain. The key reactions leading to the synthesis of the rapamycin-derived pyran fragment include the following: (i) Paterson aldol, (ii) stereoselective β-OH carbonyl reduction, and (iii) regio- and stereoselective intramolecular oxy-Michael reaction. The other piece needed for building the macrocyclic diversity was obtained from the coupling of various amino alcohol moieties with S-pipecolic acid.

Original languageEnglish
Pages (from-to)480-483
Number of pages4
JournalOrganic Letters
Volume17
Issue number3
DOIs
Publication statusPublished - 6 Feb 2015
Externally publishedYes

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