Efficient and convergent coupling route for the short-step synthesis of enantiopure 2α- and 2β-alkylated 1α,25-dihydroxy-19-norvitamin D3 analogues

Akihiro Yoshida; Keiichiro Ono; Yoshitomo Suhara; Nozomi Saito; Hiroaki Takayama; Atsushi Kittaka

doi:10.1055/s-2003-39908

Efficient and convergent coupling route for the short-step synthesis of enantiopure 2α- and 2β-alkylated 1α,25-dihydroxy-19-norvitamin D₃ analogues

Akihiro Yoshida, Keiichiro Ono, Yoshitomo Suhara, Nozomi Saito, Hiroaki Takayama, Atsushi Kittaka

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

31 Citations (Scopus)

Abstract

Novel efficient synthesis of several enantio-pure 2-alkylated 1α,25-dihydroxy-19-norvitamin D₃ analogues through radical introduction of 2-alkyl chain and C₅-C₆ position coupling using Julia-type olefination as key steps was established starting from commercially available (-)-quinic acid as a chiral pool.

Original language	English
Pages (from-to)	1175-1179
Number of pages	5
Journal	Synlett
Issue number	8
DOIs	https://doi.org/10.1055/s-2003-39908
Publication status	Published - 2003 Jan 1
Externally published	Yes

Keywords

Coupling
Julia reactions
Radical reactions
Total synthesis
Vitamin D

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1055/s-2003-39908

Cite this

@article{4dd03cde7fb246aba48b6aec239fee11,

title = "Efficient and convergent coupling route for the short-step synthesis of enantiopure 2α- and 2β-alkylated 1α,25-dihydroxy-19-norvitamin D3 analogues",

abstract = "Novel efficient synthesis of several enantio-pure 2-alkylated 1α,25-dihydroxy-19-norvitamin D3 analogues through radical introduction of 2-alkyl chain and C5-C6 position coupling using Julia-type olefination as key steps was established starting from commercially available (-)-quinic acid as a chiral pool.",

keywords = "Coupling, Julia reactions, Radical reactions, Total synthesis, Vitamin D",

author = "Akihiro Yoshida and Keiichiro Ono and Yoshitomo Suhara and Nozomi Saito and Hiroaki Takayama and Atsushi Kittaka",

year = "2003",

month = jan,

day = "1",

doi = "10.1055/s-2003-39908",

language = "English",

pages = "1175--1179",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "8",

}

TY - JOUR

T1 - Efficient and convergent coupling route for the short-step synthesis of enantiopure 2α- and 2β-alkylated 1α,25-dihydroxy-19-norvitamin D3 analogues

AU - Yoshida, Akihiro

AU - Ono, Keiichiro

AU - Suhara, Yoshitomo

AU - Saito, Nozomi

AU - Takayama, Hiroaki

AU - Kittaka, Atsushi

PY - 2003/1/1

Y1 - 2003/1/1

N2 - Novel efficient synthesis of several enantio-pure 2-alkylated 1α,25-dihydroxy-19-norvitamin D3 analogues through radical introduction of 2-alkyl chain and C5-C6 position coupling using Julia-type olefination as key steps was established starting from commercially available (-)-quinic acid as a chiral pool.

AB - Novel efficient synthesis of several enantio-pure 2-alkylated 1α,25-dihydroxy-19-norvitamin D3 analogues through radical introduction of 2-alkyl chain and C5-C6 position coupling using Julia-type olefination as key steps was established starting from commercially available (-)-quinic acid as a chiral pool.

KW - Coupling

KW - Julia reactions

KW - Radical reactions

KW - Total synthesis

KW - Vitamin D

UR - http://www.scopus.com/inward/record.url?scp=0038053150&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0038053150&partnerID=8YFLogxK

U2 - 10.1055/s-2003-39908

DO - 10.1055/s-2003-39908

M3 - Article

AN - SCOPUS:0038053150

SN - 0936-5214

SP - 1175

EP - 1179

JO - Synlett

JF - Synlett

IS - 8

ER -