SYNTHESIS OF AXIALLY DISSYMMETRIC 3,5-OCTADIENE FRAMEWORK WITH C2 CHIRALITY VIA PALLADIUM(II)-CATALYZED TWOFOLD SIGMATROPIC REARRANGEMENT

DOI: 10.1016/S0040-4039(00)86676-9

Source and publish data:

Tetrahedron Letters p. 1157 - 1160 (1988)

Update date:2022-08-05

Topics:

Authors:

Saito, Seiki

Hamano, Shin-ichi

Moriyama, Hiroshi

Okada, Keiji

Moriwake, Toshio

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1016/S0040-4039(00)86676-9

Palladium(II)-catalyzed <3,3>sigmatropic rearrangement of (4R,5R)-4,5-(bisacetoxy)-1,8-(bisbenzyloxy)-2(E),6(E)-octadiene has proceeded convergently to give (2S,7S)-2,7-(bisacetoxy)-1,8-(bisbenzyloxy)-3(E),5(E)-octadiene, translating the original chirality completely to the migration termini, which constitutes a novel synthesis of optically pure 3,5-octadiene with C₂ chirality.

Full text of DOI:10.1016/S0040-4039(00)86676-9

Products guided by the article

Product name:(4S,5S)-1,8-di-O-benzyl-2E,6E-octadiene-1,4,5,8-tetraol

Cas No:118508-99-9

R&D Labs maybe for 118508-99-9

Shanghai Massive Chemical Technology Co., Ltd.

website:http://www.massivechem.com/

Contact:+86 21 34943721

Address:Room 435, 4th floor, Building 9, No. 2568 Gudai Road,Minhang District, Shanghai,
Zhejiang Golden-Shell Pharmaceutical Co.,Ltd.

Contact:+86-576-87501888 / 87501988

Address:No.89 Zhongxing Road. Li'ao, Yuhuan, Zhejiang, China
Wuhan Fortuna Chemical Co.,Ltd

website:http://www.fortunachem.com

Contact:86-27-59207850

Address:Add: Room 2015, No.2 Building, Kaixin Mansion No.107 Jinqiao Avenue, Wuhan, China
XI'AN CHUKANG BIOTECHNOLOGY CO.,LTD

Contact:29-63685658 63685359

Address:Room 3-1202,Building 1,Oriental oasis,East of Xianning Road,Xi'an,Shaanxi 710043 P.R.China
Shanghai Cheerchem Co., Ltd.

Contact:86-21-50966856

Address:Building 5,300 Chuanzhan Road,Pudong New District,Shanghai

Relevant to this article

Effective control of ligation and geometric isomerism: direct comparison of steric properties associated with bis-mesityl and bis-diisopropylphenyl m-terphenyl isocyanides

Doi:10.1021/ic9010828
(2009)
Design and synthesis of novel 2-phenylaminopyrimidine (PAP) derivatives and their antiproliferative effects in human chronic myeloid leukemia cells

Doi:10.3390/molecules14104166
(2009)
An efficient catalyst system for Pd-catalyzed amination of [2.2]paracyclophanyl bromides

Doi:10.1021/jo901310a
(2009)
Mechanistic study of the sPLA₂-mediated hydrolysis of a thio-ester pro anticancer ether lipid

Doi:10.1021/ja901412j
(2009)
Synthesis of undecaprenyl pyrophosphate-linked glycans as donor substrates for bacterial protein N-glycosylation

Doi:10.1016/j.tet.2009.06.032
(2009)
Palladium-catalyzed intermolecular desulfinylative cross-coupling of heteroaromatic sulfinates

Doi:10.1002/chem.201204201
(2013)

Article Doi