Synthesis of kaitocephalin facilitated by three stereoselective allylic transposition reactions

Tomoya Sugai; Yuya Okuyama; Jaehyun Shin; Shunme Usui; Shoko Hisada; Ryosuke Osanai; Takeshi Oishi; Takaaki Sato; Noritaka Chida

doi:10.1246/cl.171226

Synthesis of kaitocephalin facilitated by three stereoselective allylic transposition reactions

Tomoya Sugai, Yuya Okuyama, Jaehyun Shin, Shunme Usui, Shoko Hisada, Ryosuke Osanai, Takeshi Oishi, Takaaki Sato, Noritaka Chida

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

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 S_N2¤ 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.

Original language	English
Pages (from-to)	454-457
Number of pages	4
Journal	Chemistry Letters
Volume	47
Issue number	4
DOIs	https://doi.org/10.1246/cl.171226
Publication status	Published - 2018

Keywords

Chirality transfer
Kaitocephalin
Sigmatropic rearrangement

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.171226

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title = "Synthesis of kaitocephalin facilitated by three stereoselective allylic transposition reactions",

abstract = "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.",

keywords = "Chirality transfer, Kaitocephalin, Sigmatropic rearrangement",

author = "Tomoya Sugai and Yuya Okuyama and Jaehyun Shin and Shunme Usui and Shoko Hisada and Ryosuke Osanai and Takeshi Oishi and Takaaki Sato and Noritaka Chida",

note = "Funding Information: This research was supported by a Grant-in-Aid for Scientific Research (B) from MEXT (26288018), and the Shorai Foundation for Science and Technology. Y.O. and J.S. contributed equally in this manuscript. Synthetic assistance from Mr. Naoya Furuya is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2018 The Chemical Society of Japan.",

year = "2018",

doi = "10.1246/cl.171226",

language = "English",

volume = "47",

pages = "454--457",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "Chemical Society of Japan",

number = "4",

}

TY - JOUR

T1 - Synthesis of kaitocephalin facilitated by three stereoselective allylic transposition reactions

AU - Sugai, Tomoya

AU - Okuyama, Yuya

AU - Shin, Jaehyun

AU - Usui, Shunme

AU - Hisada, Shoko

AU - Osanai, Ryosuke

AU - Oishi, Takeshi

AU - Sato, Takaaki

AU - Chida, Noritaka

N1 - Funding Information: This research was supported by a Grant-in-Aid for Scientific Research (B) from MEXT (26288018), and the Shorai Foundation for Science and Technology. Y.O. and J.S. contributed equally in this manuscript. Synthetic assistance from Mr. Naoya Furuya is gratefully acknowledged. Publisher Copyright: © 2018 The Chemical Society of Japan.

PY - 2018

Y1 - 2018

N2 - 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.

AB - 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.

KW - Chirality transfer

KW - Kaitocephalin

KW - Sigmatropic rearrangement

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U2 - 10.1246/cl.171226

DO - 10.1246/cl.171226

M3 - Article

AN - SCOPUS:85044271186

SN - 0366-7022

VL - 47

SP - 454

EP - 457

JO - Chemistry Letters

JF - Chemistry Letters

IS - 4

ER -

Synthesis of kaitocephalin facilitated by three stereoselective allylic transposition reactions

Abstract

Keywords

ASJC Scopus subject areas

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