A concise synthesis of tubuphenylalanine and epi-tubuphenylalanine via a diastereoselective Mukaiyama aldol reaction of silyl ketene acetal

Yunjeong Park, Mikyung Sim, Tong Shin Chang, Jae Sang Ryu

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

We have developed a straightforward and auxiliary-free synthetic route towards tBu-tubuphenylalanine (tBu-Tup) and tBu-epi-tubuphenylalanine (tBu-epi-Tup), which are the key components of tubulysins and their analogs. A Lewis acid-mediated diastereoselective Mukaiyama aldol reaction using silyl ketene acetal and N-Boc-l-phenylalaninal provided γ-amino-β-hydroxyl-α-methyl esters, which were deoxygenated to γ-amino-α-methyl esters under Barton-McCombie deoxygenation conditions. Notably, the desired tBu-Tup and tBu-epi-Tup were obtained in good overall yields in four steps.

Original languageEnglish
Pages (from-to)913-919
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number3
DOIs
StatePublished - 2016

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