Novel sequential sigmatropic rearrangements of allylic diols: Application to the total synthesis of ( - )-kainic acid

Katsunori Kitamoto; Mana Sampei; Yasuaki Nakayama; Takaaki Sato; Noritaka Chida

doi:10.1021/ol1026602

Novel sequential sigmatropic rearrangements of allylic diols: Application to the total synthesis of ( - )-kainic acid

Katsunori Kitamoto, Mana Sampei, Yasuaki Nakayama, Takaaki Sato, Noritaka Chida

Department of Applied Chemistry

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

45 Citations (Scopus)

Abstract

Sequential sigmatropic rearrangements (Claisen/Claisen and Claisen/Overman) of enantiopure allylic diols are described. The reactions proceeded in complete diastereoselectivity without protecting group manipulations. The sequential Claisen/Overman rearrangement was successfully applied to the total synthesis of ( - )-kainic acid.

Original language	English
Pages (from-to)	5756-5759
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	24
DOIs	https://doi.org/10.1021/ol1026602
Publication status	Published - 2010 Dec 17

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol1026602

Cite this

@article{a2cf8d2fe7f14e9ab6af44bde32c78a7,

title = "Novel sequential sigmatropic rearrangements of allylic diols: Application to the total synthesis of ( - )-kainic acid",

abstract = "Sequential sigmatropic rearrangements (Claisen/Claisen and Claisen/Overman) of enantiopure allylic diols are described. The reactions proceeded in complete diastereoselectivity without protecting group manipulations. The sequential Claisen/Overman rearrangement was successfully applied to the total synthesis of ( - )-kainic acid.",

author = "Katsunori Kitamoto and Mana Sampei and Yasuaki Nakayama and Takaaki Sato and Noritaka Chida",

year = "2010",

month = dec,

day = "17",

doi = "10.1021/ol1026602",

language = "English",

volume = "12",

pages = "5756--5759",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "24",

}

TY - JOUR

T1 - Novel sequential sigmatropic rearrangements of allylic diols

T2 - Application to the total synthesis of ( - )-kainic acid

AU - Kitamoto, Katsunori

AU - Sampei, Mana

AU - Nakayama, Yasuaki

AU - Sato, Takaaki

AU - Chida, Noritaka

PY - 2010/12/17

Y1 - 2010/12/17

N2 - Sequential sigmatropic rearrangements (Claisen/Claisen and Claisen/Overman) of enantiopure allylic diols are described. The reactions proceeded in complete diastereoselectivity without protecting group manipulations. The sequential Claisen/Overman rearrangement was successfully applied to the total synthesis of ( - )-kainic acid.

AB - Sequential sigmatropic rearrangements (Claisen/Claisen and Claisen/Overman) of enantiopure allylic diols are described. The reactions proceeded in complete diastereoselectivity without protecting group manipulations. The sequential Claisen/Overman rearrangement was successfully applied to the total synthesis of ( - )-kainic acid.

UR - http://www.scopus.com/inward/record.url?scp=78650413655&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=78650413655&partnerID=8YFLogxK

U2 - 10.1021/ol1026602

DO - 10.1021/ol1026602

M3 - Article

C2 - 21105709

AN - SCOPUS:78650413655

SN - 1523-7060

VL - 12

SP - 5756

EP - 5759

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Novel sequential sigmatropic rearrangements of allylic diols: Application to the total synthesis of ( - )-kainic acid

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this