Synthesis of Kaitocephalin Facilitated by Three Stereoselective Allylic Transposition Reactions

A stereoselective synthesis of kaitocephalin is described. The central strategy is based on chirality transfer reactions of three secondary alcohols derived from l-arabinose. The Overman rearrangement of an α,β-unsaturated ester, and intramolecular anti-type SN2′ reaction constructed a β-hydroxy-α,α...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry letters 2018-04, Vol.47 (4), p.454-457
Main Authors: Sugai, Tomoya, Okuyama, Yuya, Shin, Jaehyun, Usui, Shunme, Hisada, Shoko, Osanai, Ryosuke, Oishi, Takeshi, Sato, Takaaki, Chida, Noritaka
Format: Article
Language:English
Subjects:
Alcohols
Arabinose
Chemical synthesis
Chirality
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A stereoselective synthesis of kaitocephalin is described. The central strategy is based on chirality transfer reactions of three secondary alcohols derived from l-arabinose. The Overman rearrangement of an α,β-unsaturated ester, and intramolecular anti-type SN2′ reaction constructed a β-hydroxy-α,α-disubstituted amino acid moiety. The third chirality transfer reaction is the Ichikawa rearrangement. These stereoselective reactions successfully established the three contiguous stereocenters embedded in kaitocephalin.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.171226